Sodium Hydroxide → HCID 59272469, compound

HRID 558158Notes

Reaction equation

HRID 558158 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:24]5[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=5[C:31]([NH:34]C=O)([CH3:33])[CH3:32])=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:37])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[OH-].[Na+]>C(O)C>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:24]5[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=5[C:31]([NH2:34])([CH3:33])[CH3:32])=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:37])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86640665HCID 86640665, compound

Product 1

HCID 59272469HCID 59272469, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of N-(2-(2-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)-4-fluorophenyl)propan-2-yl)formamide (120 mg, 231 μmol) and sodium hydroxide (5 N, 10 mL, 50 mmol) in ethanol (10 mL) at 80° C. for 3 h. Dilute the mixture with ice water and extract with chloroform/IPA (3/1, 100 mL). Wash the organic phase with water/aqueous saturated sodium chloride, dry over sodium sulfate, and concentrate in vacuo. Purify the crude product by FCC (DCM to chloroform/methanol/ammonium hydroxide 7/3/0.05 as gradient) to give the title compound as a grey solid (82 mg, 75%). MS (ES) m/z 492 [M+1]+.

Workup

  1. temperatureHeat
  2. extractionextract with chloroform/IPA (3/1, 100 mL)
  3. washWash the organic phase with water/aqueous saturated sodium chloride
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate in vacuo
  6. customPurify the crude product by FCC (DCM to chloroform/methanol/ammonium hydroxide 7/3/0.05 as gradient)

Sources & evidence

ORD record
ord-443f8363a10943af9c03fc82d1b7126e
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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