5-Trifluoromethyl-1H-benzimidazole → HCID 59727095, compound

HRID 1363159Notes

Reaction equation

HRID 1363159 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C@H:7]2[N:12]1[C:20](=[O:21])[NH:19][C:18]2[C:13]1=[N:14][C:15]([N:22]1[C:26]3[CH:27]=[C:28]([C:31](F)(F)F)[CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]1)=[N:16][CH:17]=2.F[C:36]1C=CC=C2C=1OCC[C@H]2N1C(=O)NC2C1=NC(N1C3C=CC(C(F)(F)F)=CC=3N=C1)=NC=2.FC(F)(F)C1C=CC2N=CNC=2C=1>>[CH3:36][C:29]1[C:28]([CH3:31])=[CH:27][C:26]2[N:22]([C:15]3[N:14]=[C:13]4[C:18]([NH:19][C:20](=[O:21])[N:12]4[C@H:7]4[C:6]5[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=5)[O:10][CH2:9][CH2:8]4)=[CH:17][N:16]=3)[CH:23]=[N:24][C:25]=2[CH:30]=1

Participants

4

Reactant 3

HCID 3494445-Trifluoromethyl-1H-benzimidazoleHCID 59727106HCID 59727106, compoundHCID 59727130HCID 59727130, compound

Product 1

HCID 59727095HCID 59727095, compound

Procedure

9-((R)-8-Fluorochroman-4-yl)-2-(6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-one and 9-((R)-8-fluorochroman-4-yl)-2-(5-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-one. The title compound was synthesized from 5-trifluoromethylbenzimidazole (US 2004/0087601) via the procedures described in Example 25. Purification by column chromatography (2% MeOH/DCM) eluted the 6-trifluoromethyl isomer first (1H-NMR (300 MHz, CDCl3) δ 8.8 (d, 2H), 8.4 (s, 1H), 7.9 (d, 1H), 7.6 (d, 2H), 7.0 (t, 1H), 6.7 (m, 2H), 5.9 (t, 1H), 4.7 (m, 1H), 4.4 (m, 1H), 3.0 (m, 1H), 2.4 (m, 1H).) followed by the 5-trifluoromethyl isomer (1H-NMR (300 MHz, CDCl3) δ 9.0 (s, 1H), 8.4 (s, 1H), 8.1 (s, 1H), 8.0 (d, 1H), 7.6 (d, 2H), 7.0 (m, 1H), 6.8 (m, 2H), 5.9 (t, 1H), 4.7 (m, 1H), 4.4 (m, 1H), 2.9 (m, 1H), 2.4 (m, 1H).

Workup

  1. customPurification by column chromatography (2% MeOH/DCM)
  2. washeluted the 6-trifluoromethyl isomer first (1H-NMR (300 MHz, CDCl3) δ 8.8 (d, 2H), 8.4 (s, 1H), 7.9 (d, 1H), 7.6 (d, 2H), 7.0 (t, 1H), 6.7 (m, 2H), 5.9 (t, 1H), 4.7 (m, 1H), 4.4 (m, 1H), 3.0 (m, 1H), 2.4 (m, 1H).)

Sources & evidence

ORD record
ord-c0fcbb3d7f2940f991cfab08a40d46c4
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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