Acetyl chloride → HCID 86696385, 화합물

HRID 870682노트

반응식

HRID 870682 반응식
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)(C)(C)C.C(Cl)(=[O:39])C>>[C:14]([OH:35])(=[O:39])[CH3:15].[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:35])[CH2:12][CH2:13]1

참가 물질

3

반응물 2

HCID 6367Acetyl chlorideHCID 86696384HCID 86696384, 화합물

생성물 1

HCID 86696385HCID 86696385, 화합물수율 150.3%

실험 절차

The solution of tert-butyl(1-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperidin-4-yl)carbamate (47 mg, 0.1 mmol) was cooled to 0° C. and treated with acetyl chloride (225 mg, 2.86 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-aminopiperidin-1-yl)(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)phenyl)methanone acetic acid salt (34 mg, 79% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.17-8.42 (m, J=8.3 Hz, 2H), 7.86 (s, 1H), 7.63 (d, J=9.6 Hz, 1H), 7.48-7.57 (m, J=8.6 Hz, 2H), 6.74 (d, J=9.6 Hz, 1H), 3.36-3.49 (m, 3H), 1.90-1.99 (m, 9H), 1.72 (quin, J=7.3 Hz, 2H), 1.63 (br. s., 2H), 1.44-1.55 (m, 2H), 1.01 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 393.2 [(M+H)+, calcd for C22H29N6O 393.2].

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-3f2fee59eacb47249846b594d1b6d311
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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