Acetic Acid → HCID 10168473, 화합물

HRID 132895

반응식

HRID 132895 반응식
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[N:10]([CH2:23][C:24](=O)[CH2:25][N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[CH3:38])[CH2:28][CH2:27]3)[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[NH2:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO.C(Cl)Cl>[N:43]1([CH2:42][CH2:41][NH:40][CH:24]([CH2:25][N:26]2[CH2:27][CH2:28][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH2:30][CH2:31]2)[CH2:23][N:10]2[C:7]3[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][C:6]=3[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=3)=[N:11]2)[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8795AminoethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 179753971-[5-Acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-3-(4-o-tolyl-piperazin-1-yl)-propan-2-one

생성물 1

HCID 10168473HCID 10168473, 화합물

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 21226129Dichloromethane methanol용매

실험 절차

A solution of 1-[5-acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-3-(4-o-tolyl-piperazin-1-yl)-propan-2-one (54 mg, 0.1 mmol) in 1,2-dichloroethane (0.5 mL) was treated with 1-(2-aminoethyl)piperazine (26 μL, 0.2 mmol) and glacial acetic acid (34 μL, 0.6 mmol) at 25° C. and stirred for 30 min. Sodium triacetoxyborohydride (63.6 mg, 0.3 mmol) was added and the reaction mixture was stirred for an additional 4 h before it was quenched with CH2Cl2 (5 mL) and sat. NaHCO3 (5 mL). The organic layer was separated, washed with H2O (2×5 mL), dried over Na2SO4, and concentrated. Preparative TLC (silica, 10% MeOH/CH2Cl2) afforded 22 mg (35%) of a light yellow film. TLC (10% MeOH/CH2Cl2): Rf=0.2. MS (electrospray): m/z 653.3 ([M+H]+, C35H47F3N8O requires 652.4). 1H NMR (CDCl3, 400 MHz, a mixture of two rotamers): 7.78-7.60 (m, 4H), 7.18-6.82 (m, 4H), 4.88-4.30 (m, 2H), 4.23-3.90 (m, 2H), 3.85-3.70 (m, 2H), 3.22-2.85 (m, 10H), 2.85-2.30 (m, 15H), 2.30 (s, 3H), 2.21 (s, 1.5H), 2.17 (s, 1.5H).

후처리

  1. stirringthe reaction mixture was stirred for an additional 4 h before it
  2. customwas quenched with CH2Cl2 (5 mL) and sat. NaHCO3 (5 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O (2×5 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPreparative TLC (silica, 10% MeOH/CH2Cl2) afforded 22 mg (35%) of a light yellow film

출처 및 근거

ORD 기록
ord-f35ad400167540119478eb496b9098c9
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388011B2

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