Phenyl isocyanate → HCID 11375093, compound

HRID 2099597Notes

Reaction equation

HRID 2099597 reaction equation
[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[CH:20]=[C:19]([OH:22])[CH:18]=[CH:17]4)=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>CN(C)C=O>[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[CH:20]=[C:19]([O:22][C:36](=[O:37])[NH:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:18]=[CH:17]4)=[C:9]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 136360208HCID 136360208, compound

Product 1

HCID 11375093HCID 11375093, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-(2-phenyl-5-pyridin-4-yl-3H-imidazol-4-yl)-naphthalen-2-ol (31 mg, 0.085 mmol), phenyl isocyanate (11 mg, 0.094 mmol) and triethylamine (17.8 μL, 12.9 mg, 0.128 mmol) in N,N-dimethylformamide (1.5 mL) is stirred for 2 hours at room temperature. Preparative LCMS afforded phenyl-carbamic acid 8-(2-phenyl-5-pyridin-4-yl-3H-imidazol-4-yl)-naphthalen-2-yl ester (17 mg, 41% yield); 1H NMR 400 Hz (CD3OD) δ 7.01 (m, 2H), 7.25 (m, 4H), 7.39 (m, 5H), 7.45 (dd, J=2.28, 8.86 Hz, 1H), 7.53 (m, 3H), 7.72 (dd, J=7.14, 8.23 Hz, 1H), 7.83 (d, J=6.02 Hz, 1H), 7.90 (d, J=6.99 Hz, 2H), 8.10 (m, 3H), 8.19 (d, J=8.29 Hz, 1H), 8.43 (d, J=7.00 Hz, 2H); MS m/z (M+H+) 483.20.

Sources & evidence

ORD record
ord-a29e7ba290174e87933afed85c5d701d
Source dataset
uspto-grants-2009_08
Patent number
US07569593B2

Reaction notes

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