Dimethylformamide → Tert-butyl 4-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-3,3-dimethylpiperidine-1-carboxylate

HRID 877720노트

반응식

HRID 877720 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][C:17]1([CH3:30])[CH3:29].C(N(CC)C(C)C)(C)C.CN(C)C=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][C:17]3([CH3:30])[CH3:29])=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 10171391Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylateHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide2회

생성물 1

HCID 68290809Tert-butyl 4-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-3,3-dimethylpiperidine-1-carboxylate수율 67%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (310 mg, 1.129 mmol, Intermediate 2), tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate (387 mg), N,N-diisopropylethylamine (0.592 mL, 3.39 mmol) and N,N-dimethylformamide (2 mL) was pumped under vacuum and backfiled with nitrogen twice. The reaction vial was sealed and heated to 90° C. for 2 h. The mixture was diluted with water (20 mL) and extracted with ethyl acetate twice. The organic layer was washed with brine and concentrated. Silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes, gave the title compound as a brown solid (0.3510 g, 67% yield). MS (ES+) m/z: 466.1, 468.1 (M+H); LC retention time: 4.488 min (analytical HPLC Method H).

후처리

  1. customThe reaction
  2. customvial was sealed
  3. extractionextracted with ethyl acetate twice
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-01230035d9464eecaabee903fc3bdcb2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987268B2

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