Phenyl carbamate → HCID 18005181, compound

HRID 1603803Notes

Reaction equation

HRID 1603803 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[C:16](=O)([O:18]C1C=CC=CC=1)N.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[NH:33][CH2:32][CH2:31]2>C(OCC)(=O)C>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:38])[F:39])[N:33]([C:16](=[O:18])[NH:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1)[CH2:32][CH2:31]2

Participants

5

Reactant 3

HCID 69322Phenyl carbamateHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005195HCID 18005195, compound

Product 1

HCID 18005181HCID 18005181, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Amino-2-(pyridin-4-ylmethyloxy)pyridine (0.5 g, 2.5 mmol) was converted to the phenyl carbamate and treated with 5-methoxy-6-trifluoromethylindoline (0.54 g, 2.5 mmol) as in the method of Example 52. Chromatography using ethyl acetate as eluant followed by recrystallisation from ethyl acetate/petroleum ether (60-80°) afforded the title compound (0.13 g, 13%) as an off-white solid m.p. 187-189° C.

Workup

  1. customfollowed by recrystallisation from ethyl acetate/petroleum ether (60-80°)

Sources & evidence

ORD record
ord-2938293fdc9649fda2202708348d74e3
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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