Sulfuric Acid → 1-Amino-7-[4-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

HRID 1896531Notes

Reaction equation

HRID 1896531 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]3[C:15]4[CH:21]=[CH:20][C:19]([C:22]5[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=5)=[CH:18][C:16]=4[S:17][C:13]=3[C:12]([C:32]#[N:33])=[CH:11][N:10]=2)=CC=1.[OH:36]S(O)(=O)=O.C([O-])(O)=O.[Na+].[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[NH2:8][C:9]1[C:14]2[C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=4)=[CH:18][C:16]=3[S:17][C:13]=2[C:12]([C:32]([NH2:33])=[O:36])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 59198451HCID 59198451, compound

Product 1

HCID 235819921-Amino-7-[4-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

1-[(4-Methoxybenzyl)amino]-7-[4-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carbonitrile was placed in a flask cooled to 0° C. before conc. H2SO4 (excess) was added dropwise under vigorous stirring. The final mixture was warmed to room temperature and, after 1 h, poured into THF/EtOAc and aqueous NaHCO3 previously saturated with NaCl solid. After separation of the organic phase, the aqueous phase was extracted again with THF/EtOAc, and the combined organic phases were dried over MgSO4 and filtered. After evaporation of the organic solvents, the crude material was purified by a wash with Et2O to provide the title compound as a yellow solid.

Workup

  1. additionwas added dropwise under vigorous stirring
  2. customAfter separation of the organic phase
  3. extractionthe aqueous phase was extracted again with THF/EtOAc
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customAfter evaporation of the organic solvents
  7. customthe crude material was purified by
  8. washa wash with Et2O

Sources & evidence

ORD record
ord-90426fe9d1464e28b153783e6a8b6983
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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