[(S)-1-(7-Cyclopropyl-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine → HCID 178461949, compound

HRID 243401Notes

Reaction equation

HRID 243401 reaction equation
[CH:1]1([C:4]2[C:9]3[N:10]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[C:11]([C@@H:13]([NH:15][C:16]4[N:24]=[CH:23][N:22]=[C:21]5[C:17]=4[N:18]=[CH:19][N:20]5C4CCCCO4)[CH3:14])=[N:12][C:8]=3[CH:7]=[CH:6][C:5]=2[F:37])[CH2:3][CH2:2]1>Cl.CO>[CH:1]1([C:4]2[C:9]3[N:10]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[C:11]([C@@H:13]([NH:15][C:16]4[N:24]=[CH:23][N:22]=[C:21]5[C:17]=4[N:18]=[CH:19][NH:20]5)[CH3:14])=[N:12][C:8]=3[CH:7]=[CH:6][C:5]=2[F:37])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68158234[(S)-1-(7-Cyclopropyl-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178461949HCID 178461949, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

[(S)-1-(7-Cyclopropyl-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine (59 mg, 0.12 mmol) was dissolved in HCl in methanol (5 mL, 2.5M) and the reaction stirred at RT for 30 min. The reaction mixture was concentrated in vacuo and the resultant residue subjected to preparative HPLC (C18 Phenomenex column, 5-80% MeCN in water 0.1% formic acid, 20 min gradient) to yield 274 as a white solid (28 mg, 57%). 1H NMR 400 MHz (DMSO-d6): δ 12.83 (1H, br s), 8.50 (1H, br s), 8.22-7.58 (7H, m), 7.00 (1H, dd, J=11.3, 9.4 Hz), 5.66-5.20 (1H, m), 1.52 (3H, d, J=6.6 Hz), 1.32-1.21 (1H, m), 0.37-0.20 (2H, m), 1.89-0.07 (1H, m), 0.03-0.00 (1H, m), LCMS (Method K): RT=3.27 min, [M+H]+=415

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customC18 Phenomenex column, 5-80% MeCN in water 0.1% formic acid, 20 min gradient

Sources & evidence

ORD record
ord-7889a875e1af4a26abac1cc254ea5f33
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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