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Acetic Anhydride → 4-(((3S)-1-acetyl-3-piperidinyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877727
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인쇄 미리보기

반응식

HRID 877727 반응식
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28]C(C)(C)C)=O)[CH2:21]1)(=[O:3])[NH2:2].[C:33](OC(=O)C)(=O)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:20]([NH:19][C:5]2[C:6]3[N:7]([CH:10]=[C:11]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:12]=3)[N:8]=[CH:9][C:4]=2[C:1]([NH2:2])=[O:3])[CH2:21]1)(=[O:28])[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 68291570(S)-tert-butyl 3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)piperidine-1-carboxylate

생성물 1

HCID 682914384-(((3S)-1-acetyl-3-piperidinyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A suspension of (S)-6-phenyl-4-(piperidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydrochloride salt (Example 44, 12.2 mg, 0.033 mmol) in CH2Cl2 (0.3 mL) was added acetic anhydride (3.72 μL, 0.04 mmol) followed by DIPEA (0.017 mL, 0.1 mmol). The reaction was stirred for 1 h at which time the starting material had been consumed as judged by HPLC. The solvents were removed and the product purified via reverse phase preparative HPLC. LCMS: 378 (M+H)+; HPLC (conditions E): retention time=7.41 min; 1H NMR (MeOD, 400 MHz) δ 8.17 (d, J=13 Hz, 1H), 7.97 (dd, J=1.7, 12.3 Hz, 1H), 7.75 (m, 3H), 7.40 (m, 3H), 7.27 (m, 1H), 4.38 (m, 1H), 3.83-3.94 (m, 2H), 3.42 (m, 2H), 2.21 (s, 3H), 1.98 (m, 1H), 1.87 (m, 1H), 1.75 (m, 1H).

후처리

  1. customhad been consumed
  2. customThe solvents were removed
  3. customthe product purified via reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-8578a0a006fc45c39bb2a44af5512400
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987268B2

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