6-Bromo-4-methoxyquinazoline → 6-(3,12-diazatetracyclo[10.2.2.02,10.04,9]hexadeca-2(10),4,6,8-tetraen-3-yl)-1H-quinazolin-4-one

HRID 2176198Notes

Reaction equation

HRID 2176198 reaction equation
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]2[CH2:15][CH2:16][N:2]1[CH2:3][CH2:4]2.Br[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][N:22]=[C:21]2[O:28]C>>[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][N:22]=[C:21]4[OH:28])[C:6]=2[CH:5]2[CH2:4][CH2:3][N:2]1[CH2:16][CH2:15]2

Participants

3

Reactant 2

HCID 280639706-Bromo-4-methoxyquinazolineHCID 675456263,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 1785180166-(3,12-diazatetracyclo[10.2.2.02,10.04,9]hexadeca-2(10),4,6,8-tetraen-3-yl)-1H-quinazolin-4-one

Procedure

The reaction of 3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (127 mg, 0.6 mmol; Example 187A) and 6-bromo-4-methoxyquinazoline (215 mg, 0.9 mmol; ChemBridge) was performed as described in Example 68 to afford the title compound as the major product: 1H NMR (300 MHz, methanol-d4) δ ppm 1.96-2.20 (m, 4H) 2.90-2.97 (m, 1H) 3.08-3.29 (m, 4H) 4.36 (s, 2H) 7.07-7.13 (m, 3H) 7.39-7.46 (m, 1H) 7.75-7.82 (m, 1H) 7.87-7.94 (m, 1H) 8.13 (d, J=2 Hz, 1H) 8.18 (s, 1H); MS (DCI/NH3) m/z 357 (M+H)+.

Sources & evidence

ORD record
ord-74e2099695cf408485a60e5390966d08
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

Loading…