[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → HCID 178423988, compound

HRID 241125Notes

Reaction equation

HRID 241125 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13]2)(=[O:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:25][C:26]1([CH3:50])[CH2:35][CH2:34][C:33]2[N:32]=[CH:31][N:30]=[C:29]([N:36]3[CH2:42][C:41]4[CH:43]=[C:44](B(O)O)[CH:45]=[CH:46][C:40]=4[O:39][CH2:38][CH2:37]3)[C:28]=2[CH2:27]1>>[NH2:17][C@H:14]1[CH2:15][CH2:16][N:12]([S:9]([C:4]2[C:5]([OH:8])=[N:6][CH:7]=[C:2]([C:44]3[CH:45]=[CH:46][C:40]4[O:39][CH2:38][CH2:37][N:36]([C:29]5[C:28]6[CH2:27][C:26]([CH3:25])([CH3:50])[CH2:35][CH2:34][C:33]=6[N:32]=[CH:31][N:30]=5)[CH2:42][C:41]=4[CH:43]=3)[CH:3]=2)(=[O:10])=[O:11])[CH2:13]1

Participants

3

Reactant 2

HCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acidHCID 178454140HCID 178454140, compound

Product 1

HCID 178423988HCID 178423988, compound

Procedure

Prepared according to the method of example 5 by using 1,1-dimethylethyl {(3S)-1-[(5-bromo-2-hydroxypyridin-3-yl)sulfonyl]pyrrolidin-3-yl}carbamate (reagent preparation 40) 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, Methanol-d4): 8.53 (d, 2H), 8.00 (s, 1H), 7.57 (s, 1H), 7.41 (d, 1H), 7.03 (d, 1H), 5.12 (s, 2H), 4.45 (m, 1H), 4.29 (m, 1H), 3.93 (m, 1H), 3.72 to 3.55 (m, 6H), 2.85 (t, 2H), 2.56 (s, 2H), 2.35 (m, 1H), 2.06 (m, 1H), 1.69 (t, 2H), 0.93 (s, 6H); MS (EI) for C28H34N6O4S: 551 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ed97c8e648c24e099df773a8705c4fdf
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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