Acetyl chloride → HCID 86696385、化合物

HRID 870682ノート

反応式

HRID 870682 の反応式
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

参加物

3

反応物 2

HCID 6367Acetyl chlorideHCID 86696384HCID 86696384、化合物

生成物 1

HCID 86696385HCID 86696385、化合物収率 150.3%

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-3f2fee59eacb47249846b594d1b6d311
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

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