Trifluoroacetic acid → N-(2-acetamido-1-(4-chlorophenyl)ethyl)-4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 423012노트

반응식

HRID 423012 반응식
[C:1]([NH:4][CH2:5][CH:6]([NH:14][C:15]([C:17]1([NH:32]C(=O)OC(C)(C)C)[CH2:22][CH2:21][N:20]([C:23]2[C:24]3[CH:31]=[CH:30][NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:19][CH2:18]1)=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>>[C:1]([NH:4][CH2:5][CH:6]([NH:14][C:15]([C:17]1([NH2:32])[CH2:18][CH2:19][N:20]([C:23]2[C:24]3[CH:31]=[CH:30][NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:21][CH2:22]1)=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 57750392Tert-butyl 4-(2-acetamido-1-(4-chlorophenyl)ethylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate2회

생성물 1

HCID 57750364N-(2-acetamido-1-(4-chlorophenyl)ethyl)-4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide수율 103.2%

실험 절차

Tert-butyl 4-(2-acetamido-1-(4-chlorophenyl)ethylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (Intermediate 84) (97 mg, 0.17 mmol) was treated with trifluoroacetic acid (2 mL). The solution was stirred for 1 hours at room temperature. The mixture was concentrated under reduced pressure. The crude product was purified by ion exchange chromatography, using an SCX column. The residue was loaded onto the column in methanol and washed with methanol. The desired product was eluted from the column using 2M ammonia in methanol and pure fractions were evaporated to dryness to afford N-(2-acetamido-1-(4-chlorophenyl)ethyl)-4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (80 mg, quant.) as a cream dry film.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude product was purified by ion exchange chromatography
  3. washwashed with methanol
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-afae3713fde343ca99d24f4f41df968a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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