Tert-butyl 1,4-diazepane-1-carboxylate → HCID 123966372, compound
Reaction equation
Cl.Cl.[C:3]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]([CH3:39])[C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=2)[CH2:15][CH2:14]1)=[O:11].[N:46]1([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:52][CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>>[C:3]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([O:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][N:21]([CH3:39])[C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([N:49]3[CH2:50][CH2:51][CH2:52][N:46]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:47][CH2:48]3)=[O:34])=[CH:31][CH:30]=2)[CH2:17][CH2:18]1)=[O:11]Participants
3
Procedure
25 mL of 4 N hydrochloric acid-dioxane was added to the compound (1.01 g, 1.56 mmol) obtained in Example 15c, and the mixture was stirred at room temperature for 16 hours. The solvent of the reaction mixture was evaporated under reduced pressure to give crude 4-({6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}amino)benzoate dihydrochloride as a white solid. The resulting crude carboxylic acid compound and tert-butyl 1,4-diazepane-1-carboxylate (500 mg, 2.50 mmol) were used to give the title compound (240 mg; yield, 20%) as a white solid according to the method described in Example 41a.
Sources & evidence
- ORD record
- ord-fade46467bff41f89a087a74b6a9530e
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476253B2
Reaction notes
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