Potassium Carbonate → HCID 11340732, compound

HRID 1958402Notes

Reaction equation

HRID 1958402 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[N:9]=[CH:10][C:3]=12.[C:21]([O:25][C:26](=[O:35])[NH:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:21]([O:25][C:26](=[O:35])[NH:27][CH:28]1[CH2:29][CH2:30][CH:31]([NH:34][C:2]2[N:7]=[CH:6][N:5]=[C:4]3[N:8]([C:11]4[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=4)[N:9]=[CH:10][C:3]=23)[CH2:32][CH2:33]1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 218974474-Chloro-1-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 11340732HCID 11340732, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (308 mg, 1 mmol), (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (257 mg, 1.2 mmol) and potassium carbonate (166 mg, 1.2 mmol) in THF (10 mL) was stirred at rt overnight. The mixture was purified by column chromatography to provide Compound A35 as a solid (76%). 1H NMR (CDCl3, 400 MHz) δ 1.46 (s, 9H), 1.74-2.04 (m, 8H), 3.09 (s, 3H), 3.73 (s, 1H), 4.62 (s, 1H), 8.07-8.09 (m, 3H), 8.49 (s, 1H), 8.57-8.59 (m, 2H). Exact mass calculated for C23H30N6O4S 486.2, found 487.2 (MH+).

Workup

  1. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-339eb50d1b174156a855211d7f7148f4
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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