Cyclopropanecarboxaldehyde → HCID 56667334, 화합물

HRID 1645192노트

반응식

HRID 1645192 반응식
Cl.[CH:2]12[CH:7]([CH2:8][N:9]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)[C:10]([C:12]3[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=3)=[O:11])[CH:6]1[CH2:5][NH:4][CH2:3]2.[CH:30]1([CH:33]=O)[CH2:32][CH2:31]1>ClCCCl>[CH:30]1([CH2:33][N:4]2[CH2:5][CH:6]3[CH:2]([CH:7]3[CH2:8][N:9]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:28])([F:29])[F:27])[CH:20]=3)[C:10]([C:12]3[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=3)=[O:11])[CH2:3]2)[CH2:32][CH2:31]1

참가 물질

4

반응물 2

HCID 123114CyclopropanecarboxaldehydeHCID 11844910HCID 11844910, 화합물

생성물 1

HCID 56667334HCID 56667334, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a stirring solution of 1-Methyl-1H-imidazole-4-carboxylic acid (3-aza-bicyclo[3.1.0]hex-6-ylmethyl)-(3-trifluoromethoxy-benzyl)-amide Hydrochloride prepared above (0.8 gm, 1.9 mmol) in 18.5 mL of DCE at room temperature was added Cyclopropanecarbaldehyde (0.1 mL, 1.6 mmol) and NaHB(OAc)3 (0.8 gm, 3.7 mmol). The reaction stirred at room temperature for 16 hours, was quenched by the addition of saturated NaHCO3, and extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to yield the crude material, which was purified via flash chromatography with 5-30% MeOH/CH2Cl2. The product containing fractions were collected and concentrated to yield 1-Methyl-1H-imidazole-4-carboxylic acid (3-cyclopropylmethyl-3-aza-bicyclo[3.1.0]hex-6-ylmethyl)-(3-trifluoromethoxy-benzyl)-amide 0.5 gm. 400 MHz 1H NMR (CDCl3) δ 7.5 (s, 1H), 7.3 (m, 2H) 7.2-7.0 (m, 3H), 5.5 (brs, 1H) 4.8 (brs, 1H), 4.0 (brs, 1H), 3.7 (s, 3H), 3.3 (brs, 1H), 3.0 (m, 2H), 2.2 (m, 4H), 1.5 (brs, 1H), 1.3 (m, 2H), 0.8 (m, 1H), 0.4 (m, 2H), 0.0 (m, 2H); MS (M+1) 449.3.

후처리

  1. customwas quenched by the addition of saturated NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield the crude material, which
  7. customwas purified via flash chromatography with 5-30% MeOH/CH2Cl2
  8. additionThe product containing fractions
  9. customwere collected
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a25cc5f87a2e4ac2bf0b35cf1e0a91bd
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124639B2

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