Acetyl chloride → HCID 86696387, 화합물

HRID 870684노트

반응식

HRID 870684 반응식
[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:35]=[CH:34][C:18]([C:19]([N:21]4[CH2:26][CH2:25][N:24](C([O:29][C:30]([CH3:33])(C)C)=O)[CH2:23][CH2:22]4)=[O:20])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(=[O:38])C>>[C:30]([OH:38])(=[O:29])[CH3:33].[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[O:20])=[CH:34][CH:35]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

3

반응물 2

HCID 6367Acetyl chlorideHCID 86696386HCID 86696386, 화합물

생성물 1

HCID 86696387HCID 86696387, 화합물수율 84.7%

실험 절차

The solution of tert-butyl 4-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperazine-1-carboxylate (65 mg, 0.14 mmol) was cooled to 0° C. and treated with acetyl chloride (320 mg, 4.07 mmol). The reaction was maintained at room temperature for overnight. The resulting solution was concentrated under reduced pressure and the residue was purified by preparative HPLC (neutral) to afford (4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)phenyl)(piperazin-1-yl)methanone acetic acid salt (52 mg, 76% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.34 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.64 (d, J=9.6 Hz, 1H), 7.55 (d, J=8.3 Hz, 2H), 6.75 (d, J=9.6 Hz, 1H), 3.40 (t, J=7.2 Hz, 2H), 3.04 (br. s., 3H), 1.92-2.02 (m, 7H), 1.73 (t, J=7.2 Hz, 2H), 1.41-1.59 (m, 2H), 1.02 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 379.2 [(M+H)+, calcd for C21H27O 379.2].

후처리

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (neutral)

출처 및 근거

ORD 기록
ord-1120b7e6c03e4e37a96f3bdfa1584e03
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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