Cesium carbonate → HCID 178437086, compound

HRID 2168234Notes

Reaction equation

HRID 2168234 reaction equation
[CH2:1]([C:3]1[C:11]2[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[N:5](S(C2C=CC=CC=2)(=O)=O)[CH:4]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>CO.C1COCC1>[CH2:1]([C:3]1[C:11]2[C:6]([NH:7][CH:8]=[N:9][C:10]=2[N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)=[N:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 67988031HCID 67988031, compound

Product 1

HCID 178437086HCID 178437086, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-{1-[5-ethyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}benzamide D7 (174 mg) and cesium carbonate (347 mg, 1.066 mmol) in MeOH (1.5 mL) and THF (3 mL) was stirred at room temperature for 3 hours. LCMS showed loss of starting material so the mixture was partitioned between EtOAc (10 mL) and water (10 mL). The organic phase was isolated (phase separator) and then concentrated. The crude material was purified by MDAP to give E18 (6 mg), 1H NMR (d6-DMSO) δ 11.59 (1H, brs), 8.38 (1H, d), 8.24 (1H, s), 8.78 (2H, d), 7.52 (1H, t), 7.46 (2H, t), 7.09 (1H, s), 4.06 (1H, m), 3.95 (2H, d), 3.02 (2H, t), 2.77 (2H, q), 1.94 (2H, d), 1.76 (2H, ddd), 1.26 (3H, t), MS(ES+) 350 [M+H]+.

Workup

  1. customwas partitioned between EtOAc (10 mL) and water (10 mL)
  2. customThe organic phase was isolated (phase separator)
  3. concentrationconcentrated
  4. customThe crude material was purified by MDAP
  5. customto give E18 (6 mg), 1H NMR (d6-DMSO) δ 11.59 (1H, brs), 8.38 (1H, d), 8.24 (1H, s), 8.78 (2H, d), 7.52 (1H, t), 7.46 (2H, t), 7.09 (1H, s), 4.06 (1H, m), 3.95 (2H, d), 3.02 (2H, t), 2.77 (2H, q), 1.94 (2H, d), 1.76 (2H, ddd), 1.26 (3H, t), MS(ES+) 350 [M+H]+

Sources & evidence

ORD record
ord-7fb89b6fdba04599a768e380ed728bdc
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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