1-Isocyanato-4-methoxybenzene → HCID 11646389, compound

HRID 540555Notes

Reaction equation

HRID 540555 reaction equation
[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>>[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[O:27])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 231394493-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 11646389HCID 11646389, compoundYield 29%

Procedure

3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-methoxyphenylisocyanate, in a similar manner as described in Example 1.68. Additionally the residue was washed with CH2Cl2, providing 18 mg (29% yield) of Compound 87: LCMS m/z (%)=371 (M+H, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.06 (s, 1H), 7.95 (s, 1H), 7.63 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 7.49 (d, J=2.8 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.37 (d, JH,F=4.4 Hz, 1H), 7.11 (d, J=9.2 Hz, 1H), 6.85 (d, J=9.2 Hz, 2H), 3.82 (s, 3H), 3.75 (s, 3H), 3.65 (s, 3H). 19F NMR (376 MHz, acetone-d6) δ: −177.41 (d, JH,F=4.1 Hz, 1F).

Workup

  1. washAdditionally the residue was washed with CH2Cl2

Sources & evidence

ORD record
ord-cba3bd14262b4b17a329668ca4a69712
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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