Trifluoroacetic acid → 3-Chloro-4-fluoro-benzo[b]thiophene-2-carboxylic acid (4-amino-cyclohexyl)-(2-methoxy-5-pyridin-3-yl-benzyl)-amide

HRID 2389714Notes

Reaction equation

HRID 2389714 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:30]([C:32]2[S:36][C:35]3[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:34]=3[C:33]=2[Cl:42])=[O:31])[CH2:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:18][C:17]=2[O:28][CH3:29])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:18][C:17]=2[O:28][CH3:29])[C:30]([C:32]2[S:36][C:35]3[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:34]=3[C:33]=2[Cl:42])=[O:31])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59775680{4-[(3-Chloro-4-fluoro-benzo[b]thiophene-2-carbonyl)-(2-methoxy-5-pyridin-3-yl-benzyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester

Product 1

HCID 597669223-Chloro-4-fluoro-benzo[b]thiophene-2-carboxylic acid (4-amino-cyclohexyl)-(2-methoxy-5-pyridin-3-yl-benzyl)-amideYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

410 is prepared according to a method similar to Method G. {4-[(3-Chloro-4-fluoro-benzo-[b]thiophene-2-carbonyl)-(2-methoxy-5-pyridin-3-yl-benzyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester (N3) (0.93 g, 1.48 mmol) is dissolved in 10 mL methylene chloride. Trifluoroacetic acid is added (0.35 mL) and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is evaporated and pumped dry. The residue is partitioned between 5% methanol/methylene chloride and half-saturated aqueous sodium bicarbonate. The aqueous layer is extracted with 5% methanol/methylene chloride, and the combined organic extracts are dried (MgSO4), filtered and evaporated to yield an ivory solid (0.375 g, 0.717 mmol; 48% yield) that was pure by LCMS analysis.

Workup

  1. custom410 is prepared
  2. customThe reaction mixture is evaporated
  3. custompumped dry
  4. customThe residue is partitioned between 5% methanol/methylene chloride and half-saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer is extracted with 5% methanol/methylene chloride
  6. dry with materialthe combined organic extracts are dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield an ivory solid (0.375 g, 0.717 mmol; 48% yield) that

Sources & evidence

ORD record
ord-ddb16874ec114a4e9360478850910e82
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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