HCID 86711982, compound → HCID 70978432, compound

HRID 2281049Notes

Reaction equation

HRID 2281049 reaction equation
[C:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:30]=[CH:29][C:21]3[N:22]([CH2:25][CH:26]4[CH2:28][CH2:27]4)[N:23]=[N:24][C:20]=3[C:19]=2[C:31]([F:34])([F:33])[F:32])=[CH:14][CH:13]=1)[CH2:5][C:6]([O:8]CC)=O)(=[O:3])[NH2:2]>ClCCl.O>[CH:26]1([CH2:25][N:22]2[C:21]3[CH:29]=[CH:30][C:18]([C:15]4[CH:16]=[CH:17][C:12]([CH2:11][N:4]5[CH2:5][C:6](=[O:8])[NH:2][C:1]5=[O:3])=[CH:13][CH:14]=4)=[C:19]([C:31]([F:32])([F:33])[F:34])[C:20]=3[N:24]=[N:23]2)[CH2:28][CH2:27]1

Participants

4

Reactant 1

HCID 86711982HCID 86711982, compound

Product 1

HCID 70978432HCID 70978432, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl N-carbamoyl-N-{4-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]benzyl}glycinate was dissolved in a dichloromethane/1 N hydrochloric acid solution and the reaction mixture placed into an oil-bath preheated to 100° C. The mixture was stirred for 1.5 hours, cooled to ambient temperature, diluted with water and extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over sodium sulfate and concentrated in vacuo to afford the titled compound as a white solid. H1-NMR (400 MHz, CDCl3): δ 8.87 (1H, s), 7.70 (1H, d, J=8.6 Hz), 7.35 (1H, d, J=8.6 Hz), 7.30 (2H, d, J=8.3 Hz), 7.26 (2H, d, J=8.3 Hz), 4.55 (2H, s), 4.53 (2H, d, J=7.2 Hz), 3.80 (2H, s), 1.60-1.49 (1H, m), 0.69-0.57 (2H, m), 0.52-0.41 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 430.1509 [(M+H)+; calculated for C21H19F3N5O2: 430.1485].

Workup

  1. customthe reaction mixture placed into an oil-bath
  2. custompreheated to 100° C
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d20fcdd4b4f416bad7e6be5c5b47c43
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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