p-Isopropylphenyl isocyanate → HCID 11494994, compound

HRID 407422Notes

Reaction equation

[Cl: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].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>>[Cl: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:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=2)=[O:28])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

Reactant 2

HCID 94416p-Isopropylphenyl isocyanate

HCID 231395183-(4-Chloro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenylamine

Product 1

HCID 11494994HCID 11494994, compoundYield 2%

Procedure

3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-isopropylphenyl isocyanate in a similar manner as described in Example 1.53, providing 1.3 mg (2%) of Compound 76 (Note: Compound 76 did not precipitate out). Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=401 (M+H37Cl, 31), 399 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.63 (s, 1H), 8.52 (s, 1H), 7.59 (dd, J1=8 Hz, J2=4 Hz, 1H), 7.41 (d, J=2 Hz, 1H), 7.37 (dd, J1=12 Hz, J2=2 Hz, 2H), 7.33 (s, 1H), 7.17 (dd, J1=8 Hz, J2=2 Hz, 2H), 7.00 (d, J=12 Hz, 1H), 3.68 (s, 3H), 3.54 (s, 3H).

Sources & evidence

ORD record: ord-56725a19efe04820b9236f453d955f51
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754238B2

Reaction notes

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