tert-Butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)-3-methylpyrrolidin-3-ylcarbamate → 3-[(3-amino-3-methylpyrrolidin-1-yl)sulfonyl]-5-{4-[(7S)-7-ethyl-2-methyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

HRID 241124Notes

Reaction equation

HRID 241124 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([N:11]2[CH2:15][CH2:14][C:13]([NH:17]C(=O)OC(C)(C)C)([CH3:16])[CH2:12]2)(=[O:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH2:26]([C@@H:28]1[CH2:37][C:36]2[N:35]=[C:34]([CH3:38])[N:33]=[C:32]([N:39]3[CH2:45][C:44]4[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][C:43]=4[O:42][CH2:41][CH2:40]3)[C:31]=2[CH2:30][CH2:29]1)[CH3:27]>>[NH2:17][C:13]1([CH3:16])[CH2:14][CH2:15][N:11]([S:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:47]3[CH:48]=[CH:49][C:43]4[O:42][CH2:41][CH2:40][N:39]([C:32]5[C:31]6[CH2:30][CH2:29][C@H:28]([CH2:26][CH3:27])[CH2:37][C:36]=6[N:35]=[C:34]([CH3:38])[N:33]=5)[CH2:45][C:44]=4[CH:46]=3)[CH:6]=2)(=[O:9])=[O:10])[CH2:12]1

Participants

3

Reactant 2

HCID 66820310tert-Butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)-3-methylpyrrolidin-3-ylcarbamateHCID 68777066{4-[(7S)-7-ethyl-2-methyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid

Product 1

HCID 595865423-[(3-amino-3-methylpyrrolidin-1-yl)sulfonyl]-5-{4-[(7S)-7-ethyl-2-methyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

Procedure

Prepared according to the method of example 5 by using 1,1-dimethylethyl {1-[(2-amino-5-bromopyridin-3-yl)sulfonyl]-3-methylpyrrolidin-3-yl}carbamate (reagent preparation 25) and {4-[(7S)-7-ethyl-2-methyl-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): 8.37 (s, 1H), 7.97 (s, 1H), 7.41 (s, 1H), 7.29 (d, 1H), 6.94 (d, 1H), 4.64 (m, 2H), 4.27 (m, 1H), 4.05 (m, 1H), 3.94 (m, 2H), 3.47 (m, 1H), 3.31 (m, 1H), 3.12 (m, 2H), 2.81 to 2.66 (m, 2H), 2.49 (m, 1H), 2.28 (s, 3H), 2.21 (m, 1H), 1.90 (m, 1H), 1.84 (m, 2H), 1.62 (m, 1H), 1.36 (m, 2H), 1.14 (s, 3H), 1.09 (m, 1H), 0.99 (t, 3H); MS (EI) for C30H39N7O3S: 578 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b06de02289a741bca0c812eb2aeabcf8
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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