Sodium Hydroxide → 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid

HRID 641976Notes

Reaction equation

HRID 641976 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[N:17]=[CH:16][N:15]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=3[CH3:31])[C:24]([O:26]C)=[O:25])[C:14]4=[O:32])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[OH-].[Na+]>>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[N:17]=[CH:16][N:15]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=3[CH3:31])[C:24]([OH:26])=[O:25])[C:14]4=[O:32])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 68603182methyl 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

Product 1

HCID 686025473-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid

Procedure

Using an analogous procedure to that described paragraph (C) in the portion of Example 1 which is concerned with the preparation of starting material methyl 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate was hydrolysed with 1N NaOH to give 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid; NMR Spectrum: (DMSOd6) 0.42 (m, 2H), 0.68 (m, 2H), 1.15 (m, 1H), 2.16 (s, 3H), 3.07 (s, broad, 2H), 3.18 (s, 4H), 3.64 (s, broad, 2H), 4.02 (s, broad, 2H), 7.59 (m, 3H), 7.70 (m, 2H), 7.92 (s, 1H), 8.00 (d, 1H), 8.15 (s, 1H), 10.52 (s, broad, 1H), 13.06 (s, broad, 1H); Mass Spectrum: M+H+ 419.

Sources & evidence

ORD record
ord-b1890aab9daf419586454fdca36cd222
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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