Quinazoline-2-carboxylic acid → HCID 71529078, compound

HRID 715070Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:12]([NH:18][C:19]([C:21]2[CH:30]=[C:29]3[C:24]([CH:25]=[N:26][C:27]([NH:31][CH:32]4CCOC[CH2:33]4)=[N:28]3)=[CH:23][CH:22]=2)=[O:20])[C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)[CH:5]=[CH:6][C:7]=1C(F)(F)F.FC1C=C([C@@H](NC(C2C=C3C(C=NC(NC(C)C)=N3)=CC=2)=O)[C@@H]2CCCN2)C=CC=1[C:45]([F:48])([F:47])[F:46].FC1C=C([C@@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@@H]2CCCN2)C=CC=1C(F)(F)F.[Cl:109]C1C=C([C@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@@H]2CCNC2)C=CC=1F.ClC1C=C([C@@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@@H]2CCNC2)C=CC=1F.ClC1C=C([C@@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@H]2CCNC2)C=CC=1F.ClC1C=C([C@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@H]2CCNC2)C=CC=1F.ClC1C=CC([C@@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@@H]2CCCN2)=CC=1F.FC1C=C([C@@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@@H]2CCCN2)C=CC=1OC.FC1C=C([C@@H](NC(C2C=C3C(C=NC(N[C@@H](C4CC4)C)=N3)=CC=2)=O)[C@@H]2CCCN2)C=CC=1OC.FC1C=C([C@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@H]2C[C@H](F)CN2)C=CC=1OC.ClC1C=CC([C@H](NC(C2C=C3C(C=NC(NC4CCOCC4)=N3)=CC=2)=O)[C@H]2CC[C@@H](C)N2)=CC=1F.N1C2C(=CC=CC=2)C=NC=1C(O)=O>>[Cl:109][C:7]1[CH:6]=[CH:5][C:4]([C@H:12]([NH:18][C:19]([C:21]2[CH:30]=[C:29]3[C:24]([CH:25]=[N:26][C:27]([NH:31][C@@H:32]([CH3:33])[C:45]([F:48])([F:47])[F:46])=[N:28]3)=[CH:23][CH:22]=2)=[O:20])[C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[CH:3][C:2]=1[F:1]

Participants

Reactant 13

HCID 19006950Quinazoline-2-carboxylic acid

HCID 71496746HCID 71496746, compound

HCID 71528994HCID 71528994, compound

HCID 71529513HCID 71529513, compound

HCID 71529546HCID 71529546, compound

HCID 71529547HCID 71529547, compound

HCID 71529548HCID 71529548, compound

HCID 71529550HCID 71529550, compound

HCID 131734080HCID 131734080, compound

HCID 1317340812-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-trifluoromethyl-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide

HCID 131734082HCID 131734082, compound

HCID 131734083HCID 131734083, compound

HCID 131734084HCID 131734084, compound

Product 1

HCID 71529078HCID 71529078, compound

Procedure

2-(Tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-trifluoromethyl-phenyl)-(S)-pyrrolidin-2-yl-methyl]-amide (I-3), 2-isopropylamino-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-trifluoromethyl-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide (I5) 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-trifluoromethyl-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide (I-7), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(R)-(3-chloro-4-fluoro-phenyl)-(R)-pyrrolidin-3-yl-methyl]-amide (I-8), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(R)-(3-chloro-4-fluoro-phenyl)-(S)-pyrrolidin-3-yl-methyl]-amide (I-9), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-chloro-4-fluoro-phenyl)-(S)-pyrrolidin-3-yl-methyl]-amide (I-10), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-chloro-4-fluoro-phenyl)-(R)-pyrrolidin-3-yl-methyl]-amide (I-11), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(4-chloro-3-fluoro-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide (I-23), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide (I-24), 2-((R)-1-cyclopropyl-ethylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-(R)-pyrrolidin-2-yl-methyl]-amide (I-26), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-((2R,4S)-4-fluoro-pyrrolidin-2-yl)-methyl]-amide (I-31), 2-(tetrahydropyran-4-ylamino)-quinazoline-7-carboxylic acid [(S)-(4-chloro-3-fluoro-phenyl)-((2R,5R)-5-methyl-pyrrolidin-2-yl)-methyl]-amide (I-35) and 2-((S)-2,2,2-trifluoro-1-methyl-ethylamino)-quinazoline-7-carboxylic acid [(S)-(4-chloro-3-fluoro-phenyl)-(S)-pyrrolidin-2-yl-methyl]-amide (I-40) were prepared analogously from the appropriate 2-substitued quinazoline-2-carboxylic acid and the requisite amine.

Sources & evidence

ORD record: ord-120e3d7f399440b09f0b0d90384e9cba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187462B2

Reaction notes

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