3-amino-2-methylquinazolin-4(3H)-one → 2-(1-adamantyl)-N-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide

HRID 1853400Notes

Reaction equation

HRID 1853400 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH3:13].[C:14]12([CH2:24][C:25](Cl)=[O:26])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2>>[C:14]12([CH2:24][C:25]([NH:1][N:2]3[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=[C:3]3[CH3:13])=[O:26])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

3

Reactant 2

HCID 2375913-amino-2-methylquinazolin-4(3H)-oneHCID 27718821-Adamantaneacetyl chloride

Product 1

HCID 498724342-(1-adamantyl)-N-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide

Procedure

3-Amino-2-methyl-4(3H)-quinazolinone and 1-adamantaneacetyl chloride were reacted as described in Example 5 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60-1.74 (m, 9H), 1.94-1.98 (m, 3H), 2.13 (d, J=1.7 Hz, 1H), 2.39 (s, 3H), 7.50-7.56 (m, 1H), 7.63-7.65 (m, 1H), 7.82-7.88 (m, 1H), 8.11 (dd, J=8.1, 1.0 Hz, 1H), 10.87 (s, 1H) ppm; MS (DCI/NH3) m/z 352 (M+H)+; Elemental Analysis: Calculated for C20H25N3O2.H2O: C, 68.27; H, 7.37; N, 11.37. Found: C, 68.16; H, 7.40; N, 11.40.

Sources & evidence

ORD record
ord-147c21545cea48d397f657f881a12da7
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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