2,4-Diamino-6-chloropyrimidine → 6-[(1R,6S)-3-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-8-yl]pyrimidine-2,4-diamine

HRID 1193205Notes

Reaction equation

HRID 1193205 reaction equation
C12N(C3C=NC4C(=CC=CC=4)N=3)CC1CCNC2.[C@@H:19]12[NH:26][CH2:25][C@@H:24]1[CH2:23][CH2:22][N:21]([C:27]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[N:36]1[N:40]=[CH:39][CH:38]=[N:37]1)=[O:28])[CH2:20]2.Cl[C:42]1[CH:47]=[C:46]([NH2:48])[N:45]=[C:44]([NH2:49])[N:43]=1>>[F:35][C:33]1[CH:32]=[CH:31][C:30]([N:36]2[N:40]=[CH:39][CH:38]=[N:37]2)=[C:29]([C:27]([N:21]2[CH2:22][CH2:23][C@@H:24]3[C@@H:19]([N:26]([C:42]4[N:43]=[C:44]([NH2:49])[N:45]=[C:46]([NH2:48])[CH:47]=4)[CH2:25]3)[CH2:20]2)=[O:28])[CH:34]=1

Participants

4

Reactant 3

HCID 674322,4-Diamino-6-chloropyrimidineHCID 67116560(1R,6S)-3,8-diazabicyclo[4.2.0]octan-3-yl(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanoneHCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 699326746-[(1R,6S)-3-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-8-yl]pyrimidine-2,4-diamine

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, Step A, using (1R,6S)-3,8-diazabicyclo[4.2.0]octan-3-yl(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone and 4-chloro-2,6-diaminopyrimidine. MS (ESI) mass calcd. for C19H20FN9O, 409.4; m/z found, 410.2 [M+H]+.

Sources & evidence

ORD record
ord-a3a625c9568b4c3ebfa4ffa9920da961
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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