2H-pyran-4-amine → HCID 71529653, compound

HRID 715072Notes

Reaction equation

HRID 715072 reaction equation
ClC1C=CC([C@@H](C2C=CN(C)N=2)N)=CC=1F.[F:17][C:18]1[CH:19]=[C:20]([CH:26]([C:28]2[CH:32]=[N:31][N:30]([CH3:33])[N:29]=2)[NH2:27])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[F:34][C:35]1[CH:44]=[C:43]([C:45](N[C@@H](C2C=CC(OC)=C(F)C=2)C2C=NN(C)C=2)=[O:46])[CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][C:39]([NH:64][C@H:65]1[CH2:70][CH2:69][O:68][CH2:67][C@H:66]1F)=[N:40]2.FC1C=C(C(N)=O)C=C2C=1C=NC(N[C@H]1CCOC[C@H]1F)=N2.O1C=CC(N)=CC1.F[C@H]1[C@@H](N)CCOC1>>[F:34][C:35]1[CH:44]=[C:43]([C:45]([NH:27][C@@H:26]([C:20]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([F:17])[CH:19]=2)[C:28]2[CH:32]=[N:31][N:30]([CH3:33])[N:29]=2)=[O:46])[CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][C:39]([NH:64][CH:65]1[CH2:66][CH2:67][O:68][CH2:69][CH2:70]1)=[N:40]2

Participants

7

Reactant 6

HCID 177912712H-pyran-4-amineHCID 68295107HCID 68295107, compoundHCID 71247330HCID 71247330, compoundHCID 71247449HCID 71247449, compoundHCID 71529170HCID 71529170, compoundHCID 117965500HCID 117965500, compound

Product 1

HCID 71529653HCID 71529653, compound

Procedure

(S)-5-Fluoro-N-((3-fluoro-4-methoxyphenyl)(2-methyl-2H-1,2,3-triazol-4-yl)methyl)-2-(tetrahydro-2H-pyran-4-ylamino)quinazoline-7-carboxamide (I-51) was prepared analogously except 32b was replaced with 34c, and 5-fluoro-N-((S)-(3-fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-((3S,4S)-3-fluorotetrahydro-2H-pyran-4-ylamino)quinazoline-7-carboxamide (I-52) was prepared analogously except 84b was replaced with 5-fluoro-2-((3S,4S)-3-fluorotetrahydro-2H-pyran-4-ylamino)quinazoline-7-carboxamide which can be prepared in accord with the procedure in example 3 except in step 3, 2H-pyran-4-amine was replaced with 60c.

Sources & evidence

ORD record
ord-ada027c62628440baaae536faa8c130c
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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