2-(2,2-Difluoro-2-(4-fluorophenyl)acetamido)-4-methoxybenzamide → HCID 178487748, compound

HRID 1424426Notes

Reaction equation

HRID 1424426 reaction equation
FC1C(F)=C2C(=CC=1F)N=C(C1C=CC(F)=CC=1)N=C2O.FC(F)(C1C=CC(F)=CC=1)C(NC1C=C(F)C=CC=1C(N)=O)=O.[F:45][C:46]([F:68])([C:61]1[CH:66]=[CH:65][C:64]([F:67])=[CH:63][CH:62]=1)[C:47]([NH:49][C:50]1[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:51]=1[C:52]([NH2:54])=[O:53])=O>>[F:45][C:46]([F:68])([C:61]1[CH:66]=[CH:65][C:64]([F:67])=[CH:63][CH:62]=1)[C:47]1[N:54]=[C:52]([OH:53])[C:51]2[C:50](=[CH:58][C:57]([O:59][CH3:60])=[CH:56][CH:55]=2)[N:49]=1

Participants

4

Reactant 3

HCID 666114372-(2,2-Difluoro-2-(4-fluorophenyl)acetamido)-4-methoxybenzamideHCID 666115412-(2,2-Difluoro-2-(4-fluorophenyl)acetamido)-4-fluorobenzamideHCID 178517501HCID 178517501, compound

Product 1

HCID 178487748HCID 178487748, compound

Procedure

2-(Difluoro(4-fluorophenyl)methyl)-7-methoxyquinazolin-4-ol was prepared according to the procedure described in Example 20 for preparation of 2-(difluoro(4-fluorophenyl)-7-fluoroquinazolin-4-ol, substituting 2-(2,2-difluoro-2-(4-fluorophenyl)acetamido)-4-fluorobenzamide in Example 20 with 2-(2,2-difluoro-2-(4-fluorophenyl)acetamido)-4-methoxybenzamide. The crude product (˜100% yield) was taken directly to the next step. 1H NMR (300 MHz, DMSO-d6) δ 3.89 (s, 3H), 7.16 (m, 2H), 7.39 (t, 2H), 7.75 (m, 2H), 8.04 (d, 1H), 12.96 (s, 1H); LC-MS (ESI) m/z 321 (M+H)+.

Sources & evidence

ORD record
ord-aaff778c557b4d34a155e158c71297e3
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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