Acetic Acid → HCID 67385883, 화합물

HRID 912171노트

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HRID 912171 반응식
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl-].[NH4+]>ClCCl>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:48][CH:47]=2)[C:9]2[N:10]=[CH:11][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:37]=[CH:36][C:33]([CH2:34][N:53]6[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]6)=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:13][N:14]=2)=[CH:44][CH:43]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 59244394HCID 59244394, 화합물

생성물 1

HCID 67385883HCID 67385883, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-benzaldehyde (76 mg, 0.118 mmol) in dichloromethane (2 ml), 1-methylpiperazine (40 μl, 0.354 mmol), sodium triacetoxy borohydride (100 mg, 472 mmol) and acetic acid (12.6 μl, 0.236 mmol) were added, followed by stirring at room temperature for 40 hours. To the reaction mixture, saturated aqueous ammonium chloride solution was added, followed by extraction twice with ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), and dried over sodium sulfate, followed by distilling off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/2M-ammonia methanol=100/1 to 30/1), whereby bis-(4-methoxy-benzyl)-(5-{7-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl)-amine was obtained as a brown powder (44 mg, 51%).

후처리

  1. extractionfollowed by extraction twice with ethyl acetate (10 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried over sodium sulfate
  4. distillationby distilling off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/2M-ammonia methanol=100/1 to 30/1)

출처 및 근거

ORD 기록
ord-51c19c1e70594e6a968e10a17f8da791
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022205B2

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