4-Bromo-2-fluorobenzonitrile → 4-(4,4-diethyl-1-methyl-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazin-6-ylamino)-2-fluorobenzonitrile

HRID 1296499Notes

Reaction equation

HRID 1296499 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH3:11])[C:9](=[O:12])[O:8][C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]=2[CH:17]=1.Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=1>>[CH2:13]([C:7]1([CH2:15][CH3:16])[C:6]2[CH:17]=[C:2]([NH:1][C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=3)[CH:3]=[CH:4][C:5]=2[N:10]([CH3:11])[C:9](=[O:12])[O:8]1)[CH3:14]

Participants

3

Reactant 2

HCID 7360294-Bromo-2-fluorobenzonitrileHCID 692163266-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 444382694-(4,4-diethyl-1-methyl-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazin-6-ylamino)-2-fluorobenzonitrile

Procedure

Prepared from 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and 4-bromo-2-fluorobenzonitrile according to the coupling procedure described in example 2. 1H NMR (DMSO-d6): δ 9.15 (s, 1H), 7.62 (t, J=7.9 Hz, 1H), 7.24 (dd, J=8.6, 2.3 Hz, 1H), 7.11 (d, J=8.7 Hz, 1H), 7.03 (d, J=2.4 Hz, 1H), 6.76 (m, 2H), 3.29 (s, 3H), 1.99 (m, 4H), 0.81 (t, J=7.3 Hz, 6H); MS (ESI) m/z 354 ([M+H]+); MS (ESI) m/z 352 ([M−H]−); Anal. calcd for C20H20FN3O2: C, 67.97H, 5.70; N, 11.89. Found: C, 67.09; H, 5.64; N, 11.53.

Sources & evidence

ORD record
ord-e198c416b3744f08b578e0938aed435c
Source dataset
uspto-grants-2007_07
Patent number
US07247625B2

Reaction notes

Loading…