Ethyl orthoformate → HCID 66918656, compound

HRID 2354169Notes

Reaction equation

[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]2)=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12][CH3:13])=[O:11])=[O:5].[CH2:31](OC(OCC)OCC)C>>[CH3:17][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N:6]1[C:4](=[O:5])[C:3]2[C:2](=[CH:21][CH:20]=[C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]3)[CH:18]=2)[N:1]=[CH:31]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 66918950HCID 66918950, compound

Product 1

HCID 66918656HCID 66918656, compound

Procedure

Using an analogous procedure to that described in Example 1, methyl 3-{[2-amino-5-(4-isopropylpiperazin-1-yl)benzoyl]amino}-4-methylbenzoate was reacted with triethylorthoformate to give methyl 4-methyl-3-[6-(4 isopropylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate; NMR Spectrum: (DMSOd6) 1.00 (d, 6H), 2.15 (s, 3H), 2.59 (m, 4H), 2.68 (m, 1H), 3.24 (m, 4H), 3.85 (s, 3H), 7.45 (d, 1H), 7.60 (m, 3H), 7.95 (m, 1H), 8.00 (m, 1H), 8.05 (d, 1H); Mass Spectrum: M+H+ 421.

Sources & evidence

ORD record: ord-c6f0b8cb184b442e978bde11e8897a96
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750154B2

Reaction notes

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