Trifluoroacetic acid → HCID 178481618, compound

HRID 600459Notes

Reaction equation

HRID 600459 reaction equation
C(O)(C(F)(F)F)=O.Cl[C:9]1[N:17]=[C:16]([N:18]2[C:22]3[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=3[N:20]=[CH:19]2)[N:15]=[C:14]2[C:10]=1[N:11]([CH3:36])[C:12](=[O:35])[N:13]2[C@H:28]1[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]1.[CH2:37]1[C@H:41]([F:42])[CH2:40][NH:39][CH2:38]1.Cl>>[F:27][C:24]1[CH:25]=[CH:26][C:21]2[N:20]=[CH:19][N:18]([C:16]3[N:15]=[C:14]4[C:10]([N:11]([CH3:36])[C:12](=[O:35])[N:13]4[C@H:28]4[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]4)=[C:9]([N:39]4[CH2:38][CH2:37][C@H:41]([F:42])[CH2:40]4)[N:17]=3)[C:22]=2[CH:23]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 178481617HCID 178481617, compound

Product 1

HCID 178481618HCID 178481618, compound

Procedure

Light brown solid. TFA salt. Synthesized from 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-(trans-4-hydroxycyclohexyl)-7-methyl-7H-purin-8(9H)-one and S-(+)-3-fluoropyrrolidine hydrochloride, following the general procedure for displacement reactions of 6-chloropurinones with aliphatic amines. 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 8.99 (s, 1H), 8.27 (dd, 1H), 7.74 (dd, 1H), 7.15 (td, 1H), 5.47 (d, J=52.4 Hz, 1H), 4.51-4.42 (m, 1H), 4.19-3.83 (overlap of 5H), 3.65 (s, 3H), 2.68-2.42 (overlap of 3H), 2.29-2.03 (overlap of 3H), 1.97-1.90 (m, 2H), 1.62-1.49 (m, 2H); MS (EI) m/z 470.3 (MH)+.

Sources & evidence

ORD record
ord-e058986331b04a0d9faef06548d162d2
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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