Acetic Anhydride → HCID 11677004, 화합물

HRID 422623노트

반응식

HRID 422623 반응식
Cl.Cl.Cl.[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([C:20]4[N:21]=[C:22]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[N:23]5[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[C:24]=45)=[CH:15][CH:16]=3)[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(N(CC)CC)C.CN(C=O)C>[NH2:29][C:25]1[C:24]2[N:23]([C:22]([CH:30]3[CH2:35][CH2:34][N:33]([C:36](=[O:38])[CH3:37])[CH2:32][CH2:31]3)=[N:21][C:20]=2[C:14]2[CH:13]=[C:12]3[C:17]([CH:18]=[CH:19][C:10]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)=[N:11]3)=[CH:16][CH:15]=2)[CH:28]=[CH:27][N:26]=1

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 66676486HCID 66676486, 화합물

생성물 1

HCID 11677004HCID 11677004, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

1-(2-Phenyl-quinolin-7-yl)-3-piperidin-4-yl-imidazo[1,5-a]pyrazin-8-ylamine-tris HCl salt (59.0 mg, 0.1 mmol) was dissolved in triethylamine (1.0 mL) and DMF (0.5 mL). Acetic anhydride (12.0 μL, 0.1 mmol) was added and the reaction was stirred for 1 h. The reaction was concentrated in vacuo and purified by silica gel chromatography (Jones Flashmaster, 2 g/12 mL cartridge, eluting with 2% 7N NH3 in methanol/CH2Cl2). The sample was further purified using MDPS to yield 1-{4-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl}ethanone as a pale yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.95 (ddd, 1H, J=22.4, 11.2, 4.0 Hz), 2.03-2.23 (m, 6H), 2.90 (ddd, 1H, J=13.6, 13.6, 2.8 Hz), 3.19-3.32 (m, 2H), 4.01 (bd, 1H, J=13.6 Hz), 4.64 (bd, 1H, J=13.2 Hz), 5.44 (bs, 2H), 7.11 (d, 1H, J=4.8 Hz), 7.24 (d, 1H, J=5.6Hz), 7.46 (ddd, 1H, J=6.0, 2.4, 0.8 Hz), 7.50-7.54 (m, 2H), 7.86-7.94 (m, 3H), 8.16 (ddd, 2H, J=7.2, 3.6, 1.6 Hz), 8.24 (d, 1H, J=8.4 Hz), 8.38 (s, 1H); MS (ES+): m/z 463 (10) [MH+]; HPLC: tR=2.1 min (OpenLynx, polar—5 min).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by silica gel chromatography (Jones Flashmaster, 2 g/12 mL cartridge, eluting with 2% 7N NH3 in methanol/CH2Cl2)
  3. customThe sample was further purified

출처 및 근거

ORD 기록
ord-047c8a6551e74077b81b6e94929c2363
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101613B2

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