4-(Trifluoromethyl)benzylamine → 1-(1-Chloro-isoquinolin-5-yl)-3-(4-trifluoromethyl-benzyl)-urea

HRID 351284Notes

Reaction equation

HRID 351284 reaction equation
C1(O[C:8](=[O:21])[NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[C:15]3[Cl:20])C=CC=CC=1.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>CS(C)=O>[Cl:20][C:15]1[C:16]2[C:11](=[C:10]([NH:9][C:8]([NH:29][CH2:28][C:27]3[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:32])[F:33])=[CH:31][CH:30]=3)=[O:21])[CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 71382112Phenyl (1-chloroisoquinolin-5-yl)carbamate

Product 1

HCID 99997771-(1-Chloro-isoquinolin-5-yl)-3-(4-trifluoromethyl-benzyl)-ureaYield 62.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(1-Chloro-isoquinolin-5-yl)-carbamic acid phenyl ester (150 mgs, 0.5 mmol), and 4-trifluoromethyl-benzylamine (88 mgs, 0.5 mmol) were combined and stirred overnight in DMSO (4 mL) at ambient temperature. The product was purified by directly injecting the crude reaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient). The appropriate fractions were lyophilized to yield 1-(1-Chloro-isoquinolin-5-yl)-3-(4-trifluoromethyl-benzyl)-urea (118 mgs, 61%) MS (MH+) 379.9; 1H NMR (DMSO-d6) δ 4.47 (d, 2H, J=5.8 Hz), 7.21 (m, 1H), 7.56 (d, 2H, J=8.1 Hz), 7.71–7.76 (m, 3H), 7.93 (d, 1H, J=8.5), 8.01 (d, 1H, J=6.0 Hz), 8.34–8.36 (m, 2H), 8.95 (s, 1H). HPLC Rt=4.57 min (90–10% water:acetonitrile gradient, 100% pure).

Workup

  1. customThe product was purified
  2. customreaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient)

Sources & evidence

ORD record
ord-e6a4319e696346fe9d410e3e6b1cfa0a
Source dataset
uspto-grants-2007_02
Patent number
US07183411B2

Reaction notes

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