{4-[7-(Methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid → 3-{[(3S)-3-aminopyrrolidin-1-yl]sulfonyl}-5-{4-[7-(methyloxy)quinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

HRID 241144Notes

Reaction equation

HRID 241144 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][O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31]([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)=[N:32][CH:33]=[N:34]2)=[CH:29][CH:28]=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:31]5[C:30]6[C:35](=[CH:36][C:27]([O:26][CH3:25])=[CH:28][CH:29]=6)[N:34]=[CH:33][N:32]=5)[CH2:43][C:42]=4[CH:44]=3)[CH:6]=2)(=[O:9])=[O:10])[CH2:12]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 68776116(S)-tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 595861533-{[(3S)-3-aminopyrrolidin-1-yl]sulfonyl}-5-{4-[7-(methyloxy)quinazolin-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 (S)-tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ylcarbamate (reagent preparation 25) 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 and BOC group deprotection. 1H NMR (400 MHz, d6-DMSO): 8.80 (s, 1H), 8.65 (d, 1H), 8.41 (m, 2H), 8.22 (m, 1H), 8.04 (d, 1H), 7.78 (s, 1H), 7.53 (d, 1H), 7.35 (m, 2H), 6.98 (br m, 2H), 5.43 (S, 2H), 4.62 (s, 2H), 4.49 (s, 2H), 3.92 (s, 3H), 3.79 (m, 1H), 3.69 (m, 1H), 3.55-3.45 (m, 3H), 3.32 (m, 2H), 2.20 (m, 1H), 1.91 (M, 1H); MS (EI) for C27H29N7O4S: 548 (MH+).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b791523fefa74419a7d7df9f75650003
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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