(5)-(3-Fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-4-yl)methanamine → 5-Fluoro-2-(3-fluoro-propylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide

HRID 715074Notes

Reaction equation

HRID 715074 reaction equation
ClC1C=CC([C@@H](C2C=CN(C)N=2)N)=CC=1F.[F:17][C:18]1[CH:19]=[C:20]([C@@H:26]([C:28]2[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=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](O)=[O:46])[CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][C:39]([NH:48][CH2:49][CH2:50][CH2:51][F:52])=[N:40]2>>[F:17][C:18]1[CH:19]=[C:20]([C@H:26]([NH:27][C:45]([C:43]2[CH:42]=[C:41]3[C:36]([CH:37]=[N:38][C:39]([NH:48][CH2:49][CH2:50][CH2:51][F:52])=[N:40]3)=[C:35]([F:34])[CH:44]=2)=[O:46])[C:28]2[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

4

Reactant 3

HCID 71247008(5)-(3-Fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-4-yl)methanamineHCID 71247330(S)-(4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-3-yl)methanamineHCID 712476415-Fluoro-2-(3-fluoro-propylamino)-quinazoline-7-carboxylic acid

Product 1

HCID 712478825-Fluoro-2-(3-fluoro-propylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide

Procedure

5-Fluoro-2-(3-fluoro-propylamino)-quinazoline-7-carboxylic acid [(S)-(3-fluoro-4-methoxy-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide (I-59) was prepared analogously except 32b was replaced with 40f and 84b was replaced with 87b.

Sources & evidence

ORD record
ord-c7479d3786624f78a26538a3a726df42
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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