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

HRID 2389714노트

반응식

HRID 2389714 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ddb16874ec114a4e9360478850910e82
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273747B2

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