HCID 68157700, compound → HCID 178498688, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]([CH:14]3[CH2:16][CH2:15]3)[C:11]([C@@H:17]([NH:19][C:20]3[N:28]=[CH:27][N:26]=[C:25]4[C:21]=3[N:22]=[CH:23][N:24]4C3CCCCO3)[CH3:18])=[N:10][C:9]=2[CH:8]=[CH:7][C:6]=1[F:35])=[O:4]>C(Cl)Cl>[CH:14]1([N:12]2[C:13]3[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([F:35])[CH:7]=[CH:8][C:9]=3[N:10]=[C:11]2[C@@H:17]([NH:19][C:20]2[N:28]=[CH:27][N:26]=[C:25]3[C:21]=2[N:22]=[CH:23][NH:24]3)[CH3:18])[CH2:16][CH2:15]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-cyclopropyl-5-fluoro-2-{(S)-1-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-ylamino]ethyl}-3H-benzoimidazole-4-carboxylic acid methyl ester (178 mg, 0.37 mmol) in DCM was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue subjected to a second SCX-2 cartridge purification. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 386 as a white solid (36 mg, 25%). LCMS (Method K): RT 3.03 min [M+H]+ 396.04. 1H NMR (DMSO-d6, 400 MHz): δ 8.25-8.11 (2H, m), 8.03 (1H, s), 7.73 (1H, dd, J=8.81, 4.72 Hz), 7.13 (1H, t, J=9.78 Hz), 5.98 (1H, s), 3.94 (3H, s), 1.68 (3H, d, J=6.74 Hz), 1.17-0.84 (4H, m)
Workup
- washwas washed with MeOH
- concentrationconcentrated in vacuo
- customthe resulting residue subjected to a second SCX-2 cartridge purification
- concentrationconcentrated in vacuo
- customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)
Sources & evidence
- ORD record
- ord-a570872c4c434dccb891ca4112935311
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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