Diisopropylethylamine → HCID 66775648, compound

HRID 1645190Notes

Reaction equation

HRID 1645190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl.[CH3:38][N:39]1[CH:43]=[C:42]([C:44](Cl)=[O:45])[N:41]=[CH:40]1>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:14][N:15]([C:44]([C:42]2[N:41]=[CH:40][N:39]([CH3:38])[CH:43]=2)=[O:45])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:25])[F:26])[CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 51341981912468-80-5HCID 66775745HCID 66775745, compound

Product 1

HCID 66775648HCID 66775648, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 6-[(3-Trifluoromethoxy-benzylamino)-methyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester prepared above (5.9 gm, 15.4 mmol) in 192 mL of CH3CN at room temperature under N2 was added DIEA (8.0 mL, 46.1 mmol) and 1-Methyl-1H-imidazole-4-carbonyl chloride HCL (5.6 gm, 30.7 mmol). After 24 hours, reaction was quenched with H2O, extracted with EtOAc. Organic layer was then washed with a 10% Citric acid solution, H2O, NaHCO3, and brine. The combined extracts were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure, to yield 6.7 gm of 6-{[(1-Methyl-1H-imidazole-4-carbonyl)-(3-trifluoromethoxy-benzyl)-amino]-methyl}-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester 400 MHz 1H NMR (CDCl3) δ 7.8 (d, J=1.2 Hz, 1H), 7.3-7.1 (m, 5H), 5.4 (s, 1H), 4.8-4.7 (m, 1H), 4.2 (m, 1H), 3.7 (s, 1H), 3.7 (s, 3H), 3.4-3.2 (m, 3H), 1.4 (s, 9H), 1.3 (m, 2H), 0.8 (m, 1H); MS (M+1) 495.3.

Workup

  1. customreaction
  2. customwas quenched with H2O
  3. extractionextracted with EtOAc
  4. washOrganic layer was then washed with a 10% Citric acid solution, H2O, NaHCO3, and brine
  5. dry with materialThe combined extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ff8f7a451744044abad30b9f6cc7b82
Source dataset
uspto-grants-2012_02
Patent number
US08124639B2

Reaction notes

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