4-Hydroxypyrrolidine → 1-(2-((6-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)pyrrolidin-3-ol

HRID 455110Notes

Reaction equation

HRID 455110 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:17][NH:18][C:19]3[N:24]=[C:23]([N:25]4[CH2:30][CH2:29][C:28](C)([OH:31])[CH2:27]C4)[CH:22]=[CH:21][N:20]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.ClC1C=CC2N(C(CNC3N=CC=CN=3)=C(C3C=CC([F:49])=CC=3)N=2)C=1.N1CCC(O)C1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:17][NH:18][C:19]3[N:24]=[C:23]([N:25]4[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]4)[CH:22]=[CH:21][N:20]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:49])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 67027490N-((6-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-2-amineHCID 670290991-(2-((6-Chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)-4-methylpiperidin-4-ol

Product 1

HCID 670287811-(2-((6-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)pyrrolidin-3-ol

Procedure

The title compound was prepared in the same fashion as that described for compound 187 from N-((6-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-2-amine and pyrrolidin-3-ol. 1H-NMR (CDCl3, 400 MHz, δ) 8.72 (d, J=11.6 Hz, 1H), 8.32 (s, 1H), 7.78 (dd, J=5.7, 8.3 Hz, 2H), 7.66 (s, 1H), 7.61 (d, J=9.6 Hz, 2H), 7.41 (d, J=9.6 Hz, 1H), 7.26 (t, J=8.7 Hz, 2H), 6.13 (dd, J=6.3, 21.2 Hz, 1H), 5.10 (s, 2H), 4.88 (, 1H), 4.48 (d, J=36.5 Hz, 1H), 3.60 (m, 1H), 3.52 (m, 1H), 3.42 (m, 1H), 2.42 (m, 2H) ppm; m/e 439 (M+H)+.

Sources & evidence

ORD record
ord-4869aacd9ef34d639ace72caf0df619b
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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