[(S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine → HCID 178487882, compound

HRID 243399Notes

Reaction equation

HRID 243399 reaction equation
[Br:1][C:2]1[C:7]2[N:8]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:9]([C@@H:11]([NH:13][C:14]3[N:22]=[CH:21][N:20]=[C:19]4[C:15]=3[N:16]=[CH:17][N:18]4C3CCCCO3)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:35][CH3:36]>Cl.CO>[Br:1][C:2]1[C:7]2[N:8]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:9]([CH:11]([NH:13][C:14]3[N:22]=[CH:21][N:20]=[C:19]4[C:15]=3[N:16]=[CH:17][NH:18]4)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:35][CH3:36]

Participants

4

Reactant 1

HCID 68157914[(S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178487882HCID 178487882, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

[(S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine (453 mg, 0.83 mmol) was dissolved in HCl in methanol (5 mL, 2.5M) and the reaction stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the resultant residue was subjected to preparative HPLC (C18 Phenomenex column, 10-90% MeCN in water 0.1% formic acid, 20 min gradient) to yield 272 as a white solid (70 mg, 18%). 1H NMR 400 MHz 6 (DMSO-d6): 8.08 (1H, br s), 8.02 (1H, s), 7.84 (1H, br s), 7.59 (1H, d, J=8.6 Hz), 7.55-7.26 (5H, m), 7.05 (1H, d, J=9.0 Hz), 5.15 (1H, br s), 3.79 (3H, s), 1.49 (3H, d, J=6.6 Hz). LCMS (Method K): RT=3.53 min, [M+H]+=464+466

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customC18 Phenomenex column, 10-90% MeCN in water 0.1% formic acid, 20 min gradient

Sources & evidence

ORD record
ord-eca89a42fe2f4d36841ade94b46a5e22
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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