Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate → 1,2,4,5-Tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester
Reaction equation
ClC1N=C2C(C3C=C(C(F)(F)F)C=CC=3Cl)=CC=CN2N=1.[C:22]([O:26][C:27]([N:29]1[CH2:35][CH2:34][C:33]2[CH:36]=[CH:37][C:38](N)=[CH:39][C:32]=2[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[C:22]([O:26][C:27]([N:29]1[CH2:35][CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]Participants
4
Procedure
748-(2-Chloro-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-chloro-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (0.62 g, 1.87 mmol) and 7-amino-1,2,4,5-tetrahydro-3-benzazepin-3-carboxylic acid tert-butyl ester (0.59 g, 2.25 mmol), with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (0.26 g, 0.47 mmol) as the ligand in a manner analogous to Example 2d (0.089 g, 8.5%). MP=88-89° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.65 (s, 1H), 8.87 (d, 1H), 8.1 (m, 1H), 7.88 (d, 1H), 7.75 (m, 2H), 7.45 (d, 1H), 7.40 (s, 1H), 7.20 (t, 1H), 7.10 (d, 1H), 3.50 (m, 4H), 2.75 (m, 4H), 1.40 (s, 9H). MS=558 (MH)+.
Sources & evidence
- ORD record
- ord-0694127e514f448da8829622d8ceb712
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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