Tetrafluoro-m-phenylenediamine dihydrochloride → 3-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylsulfonyl]-5-{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

HRID 241140Notes

Reaction equation

HRID 241140 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH2:15]([C@@H:17]1[CH2:26][C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:27]3[CH2:33][C:32]4[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:31]=4[O:30][CH2:29][CH2:28]3)[C:20]=2[CH2:19][CH2:18]1)[CH3:16].[NH2:41][C:42]1[C:47]([S:48]([N:51]2[CH2:56][C@@H:55]3[CH2:57][C@H:52]2[CH2:53][N:54]3C(OC(C)(C)C)=O)(=[O:50])=[O:49])=[CH:46][C:45](Br)=[CH:44][N:43]=1>>[C@H:52]12[CH2:57][C@H:55]([NH:54][CH2:53]1)[CH2:56][N:51]2[S:48]([C:47]1[C:42]([NH2:41])=[N:43][CH:44]=[C:45]([C:35]2[CH:36]=[CH:37][C:31]3[O:30][CH2:29][CH2:28][N:27]([C:21]4[C:20]5[CH2:19][CH2:18][C@H:17]([CH2:15][CH3:16])[CH2:26][C:25]=5[N:24]=[CH:23][N:22]=4)[CH2:33][C:32]=3[CH:34]=2)[CH:46]=1)(=[O:49])=[O:50]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 66820686{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acidHCID 68775382(1S,4S)-tert-butyl 5-(2-amino-5-bromopyridin-3-ylsulfonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 595861603-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylsulfonyl]-5-{4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}pyridin-2-amine

Procedure

Prepared as dihydrochloride salt according to the method of example 5 by using {4-[(7S)-7-ethyl-5,6,7,8-tetrahydroquinazolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}boronic acid (reagent preparation 23) and (1S,4S)-tert-butyl 5-(2-amino-5-bromopyridin-3-ylsulfonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (reagent preparation 25) in step 1 followed by Boc deprotection. 1H NMR (400 MHz, methanol-d4): 8.65 (s, 1H), 8.52 (s, 2H), 7.74 (s, 1H), 7.53 (d, 1H), 7.08 (d, 1H), 5.24 (d, 1H), 5.14 (d, 1H), 4.56 (m, 2H), 4.46 (m, 1H), 4.36 (m, 1H), 4.21 (m, 1H), 3.69 (m, 3H), 3.53 (m, 1H), 3.38 (m, 1H), 2.99 (m, 2H), 2.74 (m, 1H), 2.42 (m, 1H), 2.05 (m, 3H), 1.83 (m, 1H), 1.47 (m, 2H), 1.24 (m, 1H), 1.01 (t, 3H); MS (EI) for C29H35N7O3S: 562 (MH+).

Sources & evidence

ORD record
ord-50a2512eea51447bab0066b86932ad1d
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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