Boron tribromide → HCID 66918915, compound

HRID 2354216Notes

Reaction equation

HRID 2354216 reaction equation
[CH:1]1([NH:4][C:5](=[O:26])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[C:17]([O:24]C)[CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:26])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[C:17]([OH:24])[CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66919034HCID 66919034, compound

Product 1

HCID 66918915HCID 66918915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using an analogous procedure to that described in paragraph (A) in the portion of Example 24 which is concerned with the preparation of starting material, 2-amino-3-methoxybenzoic acid was reacted with 3-amino-N-cyclopropyl-4-methylbenzamide to give N-cyclopropyl-3-(8-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide (AZ12304507); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.68 (m, 2H), 2.12 (s, 3H), 2.84 (m, 1H), 3.94 (s, 3H), 7.49 (m, 3H), 7.74 (d, 1H), 7.83 (s, 1H), 7.89 (d, 1H), 8.24 (s, 1H), 8.44 (s, 1H); Mass Spectrum: M+H+ 350. B) Using an analogous procedure to that described in paragraph (B) in the portion of Example 24 which is concerned with the preparation of starting material, N-cyclopropyl-3-(8-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide was reacted with a 1M solution of boron tribromide in methylene chloride to give N-cyclopropyl-3-(8-hydroxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide; Mass Spectrum: M+H+ 336.

Sources & evidence

ORD record
ord-119213d0dc5c4678a13e0aa1314689e7
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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