Tetrahydrofuran → HCID 57382932, compound

HRID 2168244Notes

Reaction equation

HRID 2168244 reaction equation
[Br:1][C:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[N:4](S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[Br:1][C:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 67988165HCID 67988165, compound2×

Product 1

HCID 57382932HCID 57382932, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N-{1-[5-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}benzamide (100 mg), D6, in methanol (1 mL) and tetrahydrofuran (2 mL) was added cesium carbonate (181 mg, 0.555 mmol) and the mixture stirred at room temperature for 3 h. The reaction mixture was partitioned between water (10 mL) and ethyl acetate (15 mL) and the organic phase dried (phase separator) and the solvent removed in vacuo. The crude material was purified by MDAP to give the title compound E29 (32 mg) as a white solid. 1H NMR (d6-DMSO) δ 12.24 (1H, s), 8.38 (1H, d), 8.29 (1H, s), 7.87 (2H, d), 7.55 (1H, s), 7.53 (1H, t), 7.46 (2H, t), 4.18 (2H, d), 4.08 (1H, m), 3.09 (2H, t), 1.94 (2H, d), 1.81 (2H, ddd), MS(ES+) 400 [M(C18H1879BrN5O)+H]+.

Workup

  1. customThe reaction mixture was partitioned between water (10 mL) and ethyl acetate (15 mL)
  2. customthe organic phase dried (phase separator)
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by MDAP

Sources & evidence

ORD record
ord-7bb609098ad04965834d0c4db2f9c8e3
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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