Ethyl orthoformate → HCID 66919016, compound

HRID 2354198Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)=[CH:4][C:3]=1[C:21]([NH:23][C:24]1[CH:29]=[C:28]([C:30]([NH:32][CH:33]2[CH2:35][CH2:34]2)=[O:31])[CH:27]=[CH:26][C:25]=1[CH3:36])=[O:22].[CH2:37](OC(OCC)OCC)C>>[CH:33]1([NH:32][C:30]([C:28]2[CH:27]=[CH:26][C:25]([CH3:36])=[C:24]([N:23]3[C:21](=[O:22])[C:3]4[C:2](=[CH:20][CH:19]=[C:5]([O:6][C@@H:7]5[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8]5)[CH:4]=4)[N:1]=[CH:37]3)[CH:29]=2)=[O:31])[CH2:34][CH2:35]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 66918960HCID 66918960, compound

Product 1

HCID 66919016HCID 66919016, compound

Procedure

Using an analogous procedure to that described paragraph (C) in the portion of Example 18 which is concerned with the preparation of starting material, tert-butyl (3R)-3-{4-amino-3-[({5-[(cyclopropylamino)carbonyl]-2-methylphenyl}amino)carbonyl]phenoxy}pyrrolidine-1-carboxylate was reacted with triethylorthoformate to give tert-butyl (3R)-3-[(3-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-oxo-3,4-dihydroquinazolin-6-yl)oxy]pyrrolidine-1-carboxylate; NMR Spectrum: (DMSOd6) 0.54 (m, 2R), 0.68 (m, 2H), 1.39 (s, 9H), 2.15 (m, 5H), 2.85 (m, 1H), 3.50 (m, 4H), 5.19 (m, 1H), 7.54 (m, 3H), 7.72 (d, 1H), 7.83 (s, 1H), 7.89 (d, 1H), 8.19 (s, 1H), 8.41 (s, 1H); Mass Spectrum: M+Na+ 527.

Sources & evidence

ORD record: ord-8f0639983cc247a89a4c14a20ba59d81
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750154B2

Reaction notes

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