Dimethylformamide → HCID 25195958, compound

HRID 1670298Notes

Reaction equation

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

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 59852850HCID 59852850, compound

Product 1

HCID 25195958HCID 25195958, compoundYield 55%

Procedure

Prepared in a manner similar to that which is described for Example 91. 1-(4-(2-Carbamoylpyridin-4-yloxy)-2-chlorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea (18 mg, 0.04 mmol) in DMF (1.0 mL) was converted to 1-(4-(2-aminopyridin-4-yloxy)-2-chlorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea (10 mg, 55% yield). 1H NMR (DMSO-d6) δ 13.47 (s, 1H), 11.26 (s, 1H), 11.08 (s, 1H), 8.37 (d, 1H, J=8.5 Hz), 7.95 (d, 1H, J=7.5 Hz), 7.88 (s, 2H), 7.62 (s, 1H), 7.35 (m, 3H), 7.17 (m, 2H), 6.64 (d, 1H, J=7.5 Hz), 6.13 (s, 1H), 3.76 (s, 2H); MS (ESI+): m/z 415.18/417.17 (M+H)+.

Workup

customPrepared in a manner similar to that which

Sources & evidence

ORD record: ord-4cf1b930fed3458d932a99b2df8cfa54
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989477B2

Reaction notes

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