5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[2-(trimethylsilyl)ethoxy]pyrimidin-4-yl}amino)thiophene-3-carboxamide → HCID 178458580, compound

HRID 386125Notes

Reaction equation

HRID 386125 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([O:25]CC[Si](C)(C)C)[N:20]=2)=[C:15]([C:32]([NH2:34])=[O:33])[CH:14]=1>CO.Cl>[F:12][C:4]1[CH:5]=[C:6]([C:8]([OH:11])([CH3:9])[CH3:10])[CH:7]=[C:2]([F:1])[C:3]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][NH:22][C:21](=[O:25])[N:20]=2)=[C:15]([C:32]([NH2:34])=[O:33])[CH:14]=1

Participants

4

Reactant 1

HCID 595257675-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[2-(trimethylsilyl)ethoxy]pyrimidin-4-yl}amino)thiophene-3-carboxamide

Product 1

HCID 178458580HCID 178458580, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[2-(trimethylsilyl)ethoxy]pyrimidin-4-yl}amino)thiophene-3-carboxamide (109 mg, 0.215 mmol) was stirred in a mixture of MeOH (10 mL) and 2N HCl (6 mL) at room temperature overnight. The solvent was removed in vacuo, saturated NaHCO3 was added and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by reverse phase HPLC (40-100% MeCN—H2O) gave the title compound as a pale yellow solid after triturating in DCM.

Workup

  1. customThe solvent was removed in vacuo, saturated NaHCO3
  2. additionwas added
  3. extractionthe reaction mixture was extracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by reverse phase HPLC (40-100% MeCN—H2O)

Sources & evidence

ORD record
ord-e86f7efe837340108723832947f24601
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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