Acetyl chloride → HCID 86696387、化合物

HRID 870684ノート

反応式

HRID 870684 の反応式
[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]

参加物

3

反応物 2

HCID 6367Acetyl chlorideHCID 86696386HCID 86696386、化合物

生成物 1

HCID 86696387HCID 86696387、化合物収率 84.7%

実験手順

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].

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-1120b7e6c03e4e37a96f3bdfa1584e03
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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