(3R,4S)-1-(4-amino-3-methoxyphenyl)-3-fluoropiperidin-4-amine → (cis)-N-(4-(4-amino-3-fluoropiperidin-1-yl)-2-methoxyphenyl)-5-chloro-4-(1H-indol-3-yl)pyrimidin-2-amine

HRID 1256057Notes

Reaction equation

HRID 1256057 reaction equation
NC1C=CC(N2CC[C@H](N)[C@H](F)C2)=CC=1OC.[NH2:18][C@@H:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]3[N:37]=[C:36]([C:38]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[NH:40][CH:39]=4)[C:35]([Cl:47])=[CH:34][N:33]=3)=[C:27]([O:48][CH3:49])[CH:26]=2)[CH2:21][C@H:20]1[F:50]>>[NH2:18][C@H:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]3[N:37]=[C:36]([C:38]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[NH:40][CH:39]=4)[C:35]([Cl:47])=[CH:34][N:33]=3)=[C:27]([O:48][CH3:49])[CH:26]=2)[CH2:21][C@H:20]1[F:50]

Participants

3

Reactant 2

HCID 58071469(3R,4S)-1-(4-amino-3-methoxyphenyl)-3-fluoropiperidin-4-amine2×HCID 66710159(trans)-N-(4-(4-amino-3-fluoropiperidin-1-yl)-2-methoxyphenyl)-5-chloro-4-(1H-indol-3-yl)pyrimidin-2-amine2×

Product 1

HCID 58071491(cis)-N-(4-(4-amino-3-fluoropiperidin-1-yl)-2-methoxyphenyl)-5-chloro-4-(1H-indol-3-yl)pyrimidin-2-amine

Procedure

Starting material: (cis)-(±)-1-(4-amino-3-methoxyphenyl)-3-fluoropiperidin-4-amine (INTERMEDIATE 65) and 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (INTERMEDIATE 2). The NMR spectra of the title compound was identical to Example 33.

Sources & evidence

ORD record
ord-bb06422b1b5b48eba619a8503ec412be
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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