3-Amino-2-isopropyl-4(3H)-quinazolinone → 2-bicyclo[3.3.1]non-9-yl-N-(2-isopropyl-4-oxoquinazolin-3(4H)-yl)acetamide

HRID 1853433Notes

Reaction equation

HRID 1853433 reaction equation
[CH:1]12[CH:9]([CH2:10][C:11](Cl)=[O:12])[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.[NH2:14][N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]1[CH:26]([CH3:28])[CH3:27]>>[CH:1]12[CH:9]([CH2:10][C:11]([NH:14][N:15]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:16]3[CH:26]([CH3:28])[CH3:27])=[O:12])[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 51882113-Amino-2-isopropyl-4(3H)-quinazolinoneHCID 86648158HCID 86648158, compound

Product 1

HCID 498730102-bicyclo[3.3.1]non-9-yl-N-(2-isopropyl-4-oxoquinazolin-3(4H)-yl)acetamide

Procedure

The product from Example 56D and 3-amino-2-isopropylquinazolin-4(3H)-one (Aldrich) were processed using the method described in Example 42C to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (d, J=6.7 Hz, 3 H) 1.24 (d, J=6.7 Hz, 3 H) 1.43-1.59 (m, 4 H) 1.65-1.95 (m, 10 H) 1.97-2.08 (m, 1 H) 2.51-2.56 (m, 2 H) 3.02-3.14 (m, 1 H) 7.53 (t, J=6.9 Hz, 1 H) 7.67 (d, J=8.3 Hz, 1 H) 7.79-7.89 (m, 1 H) 8.11 (dd, J=7.9, 1.5 Hz, 1 H) 10.94 (s, 1 H); MS (ESI+) m/z 368 (M+H)+.

Sources & evidence

ORD record
ord-b94a5a4c6b8d447fba4c306a09d30b97
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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