Cyclopropanecarboxaldehyde → HCID 56667334, compound

HRID 1645192Notes

Reaction equation

HRID 1645192 reaction equation
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

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 11844910HCID 11844910, compound

Product 1

HCID 56667334HCID 56667334, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a25cc5f87a2e4ac2bf0b35cf1e0a91bd
Source dataset
uspto-grants-2012_02
Patent number
US08124639B2

Reaction notes

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