3-amino-2-(trifluoromethyl)-4(3H)-quinazolinone → 2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-[4-oxo-2-(trifluoromethyl)quinazolin-3(4H)-yl]acetamide

HRID 1912514Notes

Reaction equation

HRID 1912514 reaction equation
[CH3:1][C:2]1([CH3:13])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][C:10](Cl)=[O:11].[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[C:26]([F:29])([F:28])[F:27]>>[CH3:1][C:2]1([CH3:13])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][C:10]([NH: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[C:26]([F:28])([F:27])[F:29])=[O:11]

Participants

3

Reactant 2

HCID 14885313-amino-2-(trifluoromethyl)-4(3H)-quinazolinoneHCID 86665150HCID 86665150, compound

Product 1

HCID 687497012-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-[4-oxo-2-(trifluoromethyl)quinazolin-3(4H)-yl]acetamide

Procedure

The product from Example 1C and 3-amino-2-(trifluoromethyl)quinazolin-4(3H)-one (Bionet) were processed using method analogous to that described in Example 1D to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.00 (d, J=9.8 Hz, 1H) 1.08 (s, 3H) 1.23 (d, J=5.1 Hz, 3H) 1.85-2.05 (m, 5H) 2.06-2.24 (m, 1H) 2.31-2.45 (m, 2H) 2.53-2.61 (m, 2H) 2.62-2.76 (m, 1H) 7.58 (s, 1H) 7.60-7.68 (m, 1H) 7.88 (d, J=3.7 Hz, 1H) 8.31 (d, J=7.8 Hz, 1H); MS (ESI+) m/z 394 (M+H)+.

Sources & evidence

ORD record
ord-fc4fa05735b34c409d88e2df89157b54
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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