[4-(6,6,8-Trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → 3-{[(3R)-3-aminopyrrolidin-1-yl]sulfonyl}-5-[4-(6,6,8-trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-2-amine

HRID 241141Notes

Reaction equation

HRID 241141 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([N:11]2[CH2:15][CH2:14][C@@H:13]([NH:16]C(=O)OC(C)(C)C)[CH2:12]2)(=[O:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:25][C:26]1([CH3:51])[CH:35]=[C:34]([CH3:36])[C:33]2[N:32]=[CH:31][N:30]=[C:29]([N:37]3[CH2:43][C:42]4[CH:44]=[C:45](B(O)O)[CH:46]=[CH:47][C:41]=4[O:40][CH2:39][CH2:38]3)[C:28]=2[CH2:27]1>>[NH2:16][C@@H:13]1[CH2:14][CH2:15][N:11]([S:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:45]3[CH:46]=[CH:47][C:41]4[O:40][CH2:39][CH2:38][N:37]([C:29]5[C:28]6[CH2:27][C:26]([CH3:25])([CH3:51])[CH:35]=[C:34]([CH3:36])[C:33]=6[N:32]=[CH:31][N:30]=5)[CH2:43][C:42]=4[CH:44]=3)[CH:6]=2)(=[O:9])=[O:10])[CH2:12]1

Participants

3

Reactant 2

HCID 66820248[4-(6,6,8-Trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acidHCID 68774110(R)-tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 595863633-{[(3R)-3-aminopyrrolidin-1-yl]sulfonyl}-5-[4-(6,6,8-trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]pyridin-2-amine

Procedure

Synthesized according to the method of example 5 using (R)-tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ylcarbamate (reagent preparation 25) and [4-(6,6,8-trimethyl-5,6-dihydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1 and BOC group deprotection. 1H NMR (400 MHz, d6-DMSO): 8.54 (s, 1H), 8.48 (br s, 1H), 8.01 (d, 1H), 8.58 (d, 1H), 7.47 (dd, 1H), 7.02 (d, 1H), 6.76 (br s, 2H), 5.99 (d, 1H), 4.60 (s, 2H), 4.32 (m, 2H), 383 (m, 2H), 3.40-3.32 (m, 4H), 3.30-3.26 (m, 2H), 2.90 (m, 1H), 2.70 (s, 2H), 1.97 (s, 3H), 1.89 (s, 6H), 1.63 (m, 1H), 0.93 (s, 6H); MS (EI) for C29H35N7O3S: 562 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-a837aa82f3d9427aa7513eab5f4dd5fa
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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