5-Amino-2-chloro-4-fluorophenol → HCID 22624944, compound

HRID 1384648Notes

Reaction equation

HRID 1384648 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:21][C:22]1[C:28]([OH:29])=[CH:27][C:25]([NH2:26])=[C:24]([F:30])[CH:23]=1>>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:26][C:25]3[CH:27]=[C:28]([OH:29])[C:22]([Cl:21])=[CH:23][C:24]=3[F:30])=[N:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 226250837-Benzyloxy4-chloroquinazoline hydrochloride

Product 1

HCID 22624944HCID 22624944, compoundYield 94.2%

Procedure

Using an analogous procedure to that described in Example 70, 7-benzyloxy-4-chloroquinazoline hydrochloride (307 mg, 1 mmol), (prepared as described for the starting material in Example 70), was treated with 4-chloro-2-fluoro-5-hydroxyaniline (193 mg, 1.2 mmol), (EP 061741 A2), to give 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)quinazoline hydrochloride (407 mg, 94%). m.p. 253-257° C. 1H NMR Spectrum: (DMSOd6) 5.37(s, 2H); 7.16(d, 1H); 7.32-7.5(m, 4H); 7.54(s, 1H); 7.56(d, 2H); 7.59(dd, 1H); 8.73(d, 1H); 8.86(s, 1H); 10.63(br s, 1H); 11.6(br s, 1H) MS-ESI: 396 [MH]+

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-bfc51ea38a364d35be4273fe3a18e29e
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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