Benzimidazole → HCID 86622937, compound

HRID 2074156Notes

Reaction equation

HRID 2074156 reaction equation
N1C2C=CC=CC=2N[CH:2]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[NH:18][C:19]1[N:27]=[C:26]2[C:22]([NH:23][C:24](=[O:34])[N:25]2[CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[C:21]([Cl:35])[N:20]=1>>[Cl:35][C:21]1[N:20]=[C:19]([N:18]2[C:12]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:2]2)[N:27]=[C:26]2[C:22]=1[NH:23][C:24](=[O:34])[N:25]2[CH:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 5798BenzimidazoleHCID 86622938HCID 86622938, compound

Product 1

HCID 86622937HCID 86622937, compoundYield 46%

Procedure

Pale yellow solid. 46% yield on 2 steps (reduction and benzimidazole closing), on 2.47 mmol scale. Synthesized from 2-(2-amino-5-chlorophenylamino)-6-chloro-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one. 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 9.08 (s, 1H), 8.61 (s, 1H), 7.74 (d, 1H), 7.40 (d, 1H), 4.65-4.58 (m, 1H), 4.23-4.19 (m, 2H), 3.62 (appt, 2H), 2.82-2.76 (m, 2H), 1.93 (br d, 2H); MS (EI) m/z 405.2 (MH)+.

Sources & evidence

ORD record
ord-ecfb42757a914c19b2ec185f5feb4327
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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