Potassium Carbonate → HCID 178521590, compound

HRID 1926653Notes

Reaction equation

HRID 1926653 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[N:21][NH:22][CH:23]=4)[CH:18]=[C:13]3[C:12]([C:24]3[N:29]=[C:28]([NH:30][C@H:31]4[CH2:36][CH2:35][C@H:34]([OH:37])[CH2:33][CH2:32]4)[CH:27]=[N:26][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[NH:21]1[CH:20]=[C:19]([C:17]2[CH:18]=[C:13]3[C:12]([C:24]4[N:29]=[C:28]([NH:30][C@H:31]5[CH2:32][CH2:33][C@H:34]([OH:37])[CH2:35][CH2:36]5)[CH:27]=[N:26][CH:25]=4)=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)[CH:23]=[N:22]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178527314HCID 178527314, compound

Product 1

HCID 178521590HCID 178521590, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-4-({6-[1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl)amino}cyclohexanol (0.63 g, 0.12 mmol) in MeOH (1.3 mL) was added potassium carbonate (0.051 g, (0.37 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with MeOH (10 mL) and CH2Cl2 (10 mL), silica gel was added and concentrated to a crude residue. The residue was purified by silica gel chromatography (MeOH/CH2Cl2 gradient) to afford trans-4-({6-[5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl)amino}cyclohexanol as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 12.95 (s, 1H); 11.99 (s, 1H); 8.75 (s, 1H); 8.53 (s, 1H); 8.19 (s, 1H); 8.14 (d, 1H); 7.92 (s, 1H); 7.64 (s, 1H); 6.79 (d, 1H); 4.49 (d, 1H); 3.79 (br s, 1H); 3.43 (br s, 1H); 1.83 (br s, 2H); 1.31 (br s, 2H); 1.26 (q, 4H). LRMS (ESI) calculated for C20H21N7O [M+H]+, 376.2; found 376.1.

Workup

  1. additionwas added
  2. concentrationconcentrated to a crude residue
  3. customThe residue was purified by silica gel chromatography (MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-75ec518bdd0b404097fe86ab4ca24aa1
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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