Acetic Acid → HCID 68288342, 화합물

HRID 541462노트

반응식

HRID 541462 반응식
[CH3:1][C:2]1([CH3:35])[CH2:7][NH:6][CH2:5][C:4]2[NH:8][C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)=[O:17])=[N:10][C:3]1=2.C(O)(=O)C.[Na].[CH3:41][C:42]([CH3:44])=O>CN(C=O)C>[CH:42]([N:6]1[CH2:7][C:2]([CH3:35])([CH3:1])[C:3]2[N:10]=[C:9]([C:11]3[C:12]([CH3:34])=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=4)[CH2:22][CH2:23]3)=[O:17])[NH:8][C:4]=2[CH2:5]1)([CH3:44])[CH3:41]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5360545SodiumHCID 68352705HCID 68352705, 화합물

생성물 1

HCID 68288342HCID 68288342, 화합물수율 8.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(1-(5-(7,7-Dimethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (0.12 g, 0.26 mmol) (intermediate prepared in the synthesis of compound 451), DMF (4 mL), acetic acid (69 μL, 1.21 mmol), sodium triacetoxyborohydide (0.11 g, 0.52 mmol) and acetone (0.50 mL, 6.8 mmol) were mixed and stirred at room temperature for 2 hours. The reaction was carefully quenched with water (10 mL) and the mixture was extracted with ethyl acetate (60 mL) and the organics was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by preparative TLC (DCM/10% MeOH) followed by a second preparative TLC (ethyl acetate/5% MeOH) to obtain the title compound as a white powder (4.1 mg, 8.1%). m/z (ES+) 510 (M+H)+.

후처리

  1. additionwere mixed
  2. customThe reaction was carefully quenched with water (10 mL)
  3. extractionthe mixture was extracted with ethyl acetate (60 mL)
  4. dry with materialthe organics was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative TLC (DCM/10% MeOH)

출처 및 근거

ORD 기록
ord-7720758174c24b4e8b59e6ce3753bcca
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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