Water → HCID 178480103, compound

HRID 2168249Notes

Reaction equation

HRID 2168249 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:14]([N:16]4[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:30])[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:18][CH2:17]4)=[N:13][CH:12]=[N:11][C:10]=3[N:9](S(C3C=CC=CC=3)(=O)=O)[CH:8]=2)[CH:4]=[N:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O.O>CO.C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10]([NH:11][CH:12]=[N:13][C:14]=3[N:16]3[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:18][CH2:17]3)=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 67988169HCID 67988169, compound

Product 1

HCID 178480103HCID 178480103, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-{1-[5-(1-methyl-1H-pyrazol-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}benzamide D27 (160 mg) and cesium carbonate (285 mg, 0.88 mmol) in MeOH (2 ml) and THF (4 ml) was stirred under nitrogen at room temperature for 1 hour. EtOAc was added followed by water and the aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and concentrated to give crude product. This was purified by TLC preparation eluting with EtOAc to give 50 mg of desired product E40. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give crude product
  6. customThis was purified by TLC preparation
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-3d2f318d29364da5856bef3103d54d63
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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