{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid → (2S)-3-[(2-amino-5-{4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-3-yl)sulfinyl]-2-methylpropan-1-ol

HRID 241134Notes

Reaction equation

HRID 241134 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([CH2:10][C@@H:11]([CH3:14])[CH2:12][OH:13])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([N:28]3[CH2:34][C:33]4[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:32]=4[O:31][CH2:30][CH2:29]3)=[N:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1>>[NH2:1][C:2]1[C:7]([S:8]([CH2:10][C@@H:11]([CH3:14])[CH2:12][OH:13])=[O:9])=[CH:6][C:5]([C:36]2[CH:37]=[CH:38][C:32]3[O:31][CH2:30][CH2:29][N:28]([C:22]4[C:21]5[C:26](=[CH:27][C:18]([O:17][CH3:16])=[CH:19][CH:20]=5)[N:25]=[CH:24][N:23]=4)[CH2:34][C:33]=3[CH:35]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 66820289{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acidHCID 68774493(2S)-3-[(2-amino-5-bromopyridin-3-yl)sulfinyl]-2-methylpropan-1-ol

Product 1

HCID 57389825(2S)-3-[(2-amino-5-{4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-3-yl)sulfinyl]-2-methylpropan-1-ol

Procedure

Prepared according to the method of example 5 by using (2S)-3-[(2-amino-5-bromopyridin-3-yl)sulfinyl]-2-methylpropan-1-ol (reagent preparation 41) and {4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, Methanol-d4): 8.42 (s, 1H), 8.36 (br, 1H), 8.02 (br, 1H), 7.93 (d, 1H), 7.52 (br, 1H), 7.40 (d, 1H), 7.08 (m, 2H), 7.01 (d, 1H), 5.03 (s, 2H), 4.43 (m, 2H), 4.22 (m, 2H), 3.90 (s, 3H), 3.64 (dd, 0.5H), 3.57 to 3.46 (m, 1.5H), 3.40 (dd, 0.5H), 3.14 (dd, 0.5H), 3.01 (dd, 0.5H), 2.82 (dd, 0.5H), 2.15 (m, 1H), 1.12 (dd, 3H); MS (EI) for C27H29N5O4S: 520 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a4949ea0da7e42b1bef6ad748cc961de
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…