Sodium Bicarbonate → HCID 178424636, 화합물

HRID 1851297노트

반응식

HRID 1851297 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:9][N:10]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:12]=2)[N:3]=1.C1([C:22]2[CH:29]=[C:28]([C:30]3[C:35]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)=[CH:34][N:33]4[N:43]=[CH:44][N:45]=[C:32]4[N:31]=3)[CH:27]=[CH:26][C:23]=2[CH:24]=O)CC1.[BH-](O[C:56]([CH3:58])=O)(OC(C)=O)OC(C)=O.[Na+].[C:60]([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.C(N(CC)CC)C>[CH:58]1([C:44]2[N:45]=[C:32]3[N:31]=[C:30]([C:28]4[CH:29]=[CH:22][C:23]([CH2:24][N:16]5[CH2:17][CH2:18][CH:13]([C:11]6[N:12]=[C:8]([C:4]7[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=7)[NH:9][N:10]=6)[CH2:14][CH2:15]5)=[CH:26][CH:27]=4)[C:35]([C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)=[CH:34][N:33]3[N:43]=2)[CH2:56][CH2:60]1

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030522-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeHCID 178424635HCID 178424635, 화합물

생성물 1

HCID 178424636HCID 178424636, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8471Triethylamine용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

154 mg (0.49 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 4.2 mL NMP. After addition of 0.16 mL triethylamine the reaction mixture is stirred for one hour. 350 mg (50% pure) 2-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.05 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 113 mg (0.54 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is treated with saturated NaHCO3 and stirred for 20 minutes. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 192.2 mg (63.8%) of the desired product are obtained.

후처리

  1. stirringThe reaction mixture is stirred over night at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. stirringstirred for 20 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-c33aa09a4b004be08ecfa1bbe94b705f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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