7-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one → 7-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 241117Notes

Reaction equation

HRID 241117 reaction equation
Br[C:2]1[CH:11]=[N:10][C:9]2[NH:8][C:7](=[O:12])[CH2:6][O:5][C:4]=2[CH:3]=1.[CH3:13][C:14]1([CH3:38])[CH2:23][CH2:22][C:21]2[N:20]=[CH:19][N:18]=[C:17]([N:24]3[CH2:30][C:29]4[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:28]=4[O:27][CH2:26][CH2:25]3)[C:16]=2[CH2:15]1>>[CH3:13][C:14]1([CH3:38])[CH2:23][CH2:22][C:21]2[N:20]=[CH:19][N:18]=[C:17]([N:24]3[CH2:30][C:29]4[CH:31]=[C:32]([C:2]5[CH:11]=[N:10][C:9]6[NH:8][C:7](=[O:12])[CH2:6][O:5][C:4]=6[CH:3]=5)[CH:33]=[CH:34][C:28]=4[O:27][CH2:26][CH2:25]3)[C:16]=2[CH2:15]1

Participants

3

Reactant 2

HCID 159259837-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-oneHCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid

Product 1

HCID 668202167-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Procedure

Prepared according to the method of example 5 by using 7-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one and [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, DMSO-d6): 8.38 (s, 1H), 8.21 (s, 1H), 7.70 (s, 1H), 7.62 (s, 1H), 7.53 (d, 1H), 7.07 (d, 1H), 4.68 (s, 2H), 4.62 (s, 2H), 4.33 (m, 2H), 3.82 (m, 2H), 2.71 (t, 2H), 2.45 (s, 2H), 1.56 (t, 2H), 0.84 (s, 6H); MS (EI) for C26H27N5O3: 458 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9fbb50cf6bdb47d7a95f111b762aa055
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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