Cyclopropylamine → 6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-cyclopropyl-3-pyridinecarboxamide
Reaction equation
[C:1]([C:8]1NC=CN=1)([C:3]1[NH:4]C=CN=1)=O.[CH:13]1([N:17]2[CH2:23][CH2:22][C:21]3[CH:24]=[CH:25][C:26]([O:28][C:29]4[N:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][CH:30]=4)=[CH:27][C:20]=3[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14]1.C1(N)CC1>ClCCl>[CH:13]1([N:17]2[CH2:23][CH2:22][C:21]3[CH:24]=[CH:25][C:26]([O:28][C:29]4[N:34]=[CH:33][C:32]([C:35]([NH:4][CH:3]5[CH2:1][CH2:8]5)=[O:37])=[CH:31][CH:30]=4)=[CH:27][C:20]=3[CH2:19][CH2:18]2)[CH2:14][CH2:15][CH2:16]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Carbonyl diimidazole (142 mg, 0.88 mmol) was added to a stirred solution of 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinecarboxylic acid (E196b) (150 mg, 0.44 mmol) in dichloromethane (5 ml). After stirring at room temperature for 3 hours, cyclopropylamine (0.15 ml, 2.2 mmol) was added and the mixture was allowed to stir for a further 18 hours. The reaction mixture was applied to a SCX ion cartridge (Varian bond-elute, 10 g) and washed with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The combined basic fractions were concentrated in vacuo to afford the title compound (E196). MS (ES+) m/e 378 [M+H]+.
Workup
- stirringto stir for a further 18 hours
- washwashed with methanol
- additiona mixture of 0.880 ammonia:methanol (1:9)
- concentrationThe combined basic fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-4555693a1a3b48c193195e0bc3fc0f34
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207331B2
Reaction notes
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