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Acetyl chloride → HCID 178474044, 화합물

HRID 51587
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HRID 51587 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[CH2:27][CH2:26]3)[CH:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:38](Cl)(=[O:40])[CH3:39]>N1C=CC=CC=1.ClCCl>[C:9]([OH:40])(=[O:8])[CH3:14].[NH2:24][C:22]1[C:23]2[C:15]([C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[C:2]([NH:1][C:38](=[O:40])[CH3:39])[CH:3]=3)=[CH:16][N:17]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]4)[CH2:27][CH2:26]3)[C:18]=2[N:19]=[CH:20][N:21]=1
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참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 178480942HCID 178480942, 화합물

생성물 1

HCID 178474044HCID 178474044, 화합물수율 62.3%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A mixture of trans-5-(3-amino-4-phenoxyphenyl)-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (120 mg, 0.241 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was cooled to 0° C. then treatd with acetyl chloride (25 mg, 0.3 mmol). The mixture was warmed to ambient temperature for one hour then the solvents were removed under reduced pressure and the residue purified by preparative RP-HPLC to give trans-N1-(5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxyphenyl)acetamide acetate (45 mg, 35%): 1H NMR (DMSO-d6, 400 MHz) δ 9.67 (bs, 1H), 8.11(s, 1H), 8.00(s, 1H), 7.40(t, 3H), 7.17(m, 2H), 7.05(d, 2H), 6.95(d, 1H), 6.30(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.14(s, 3H), 2.04(s, 3H), 1.8-2.0(m, 6H), 1.89(s, 3H), 1.44(m, 2H); MS MH+540.5; RP-HPLC (Hypersil HS, 5 μm, 1000 A, 4.6×250 mm; 5%-50% acetonitrile—0.05 M ammonium acetate over 25 min, 1 ml/min) tr 20.37 min.

후처리

  1. temperatureThe mixture was warmed to ambient temperature for one hour
  2. customthe solvents were removed under reduced pressure
  3. customthe residue purified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-c4eb268dcbfd4bfeba0d504d7521a8d3
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06713474B2

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