p-(Trifluoromethoxy)phenyl isocyanate → [4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl)-phenyl)-cyclohexyl]-acetic acid

HRID 1404260Notes

Reaction equation

HRID 1404260 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[N:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)=[C:26]=[O:27]>C(Cl)Cl>[F:36][C:35]([F:37])([F:38])[O:34][C:31]1[CH:30]=[CH:29][C:28]([NH:25][C:26](=[O:27])[NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH:8]4[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:2])=[O:24])[CH2:6][CH2:7]4)=[CH:12][CH:13]=3)=[N:18][CH:19]=2)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Product 1

HCID 57899110[4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl)-phenyl)-cyclohexyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 mg (0.5 mmol) {4-[4-(5-Amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester in 5 mL DCM, 102 mg (0.5 mmol) 1-Isocyanato-4-trifluoromethoxy-benzene was added and the resulting mixture was stirred at room temperature over night. Dilution of reaction mixture with hexanes caused desired product to precipitate which was collected by filtration to afford [4-(4-{5-[3-(4-Trifluoromethoxy-phenyl)-ureido]-pyridin-2-yl}-phenyl)-cyclohexyl]-acetic acid methyl ester: M+1=528.2. 1H NMR (400 MHz, DMSO-D6) ppm 1.09-1.20 (m, 2 H) 1.50 (td, J=12.63, 10.11 Hz, 2 H) 1.80 (s, 3 H)1.83 (d, J=3.28 Hz, 2 H) 2.25 (d, J=6.82 Hz, 2 H) 2.51-2.54 (m, 1 H) 3.61 (s, 3 H) 7.31 (dd, J=8.72, 3.16 Hz, 4 H) 7.55-7.61 (m, 2 H) 7.86 (d, J=8.59 Hz, 1 H) 7.94 (d, J=8.34 Hz, 2 H) 8.02 (dd, J=8.72, 2.65 Hz, 1H) 8.66 (d, J=2.78 Hz, 1 H) 8.99 (s, 1 H) 9.05 (s, 1 H).

Sources & evidence

ORD record
ord-4ecf5f0fb61b457991e1cab1ee9aa1de
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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