Formaldehyde → HCID 18426185, compound
Reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:7]=1[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=[O:13])=[O:9].[CH2:35]=O.O.[OH-].[Na+]>C(#N)C.ClCCl.CO.C(O)(=O)C>[Br:34][C:31]1[CH:32]=[CH:33][C:6]([N:2]([CH3:1])[CH3:35])=[C:7]([CH:30]=1)[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=[O:13])=[O:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
Sodium cyanoborohydride (26 mg, 0.42 mmol) and acetic acid (14 μL) was added successively to a mixture of 4-{N-(2-amino-5-bromobenzoyl)glycyl}aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1042) (67 mg, 0.14 mmol), 37% formaldehyde solution in water (0.112 mL, 1.4 mmol), acetonitrile (2 mL), and methanol (1.5 mL). After the solution was stirred at 50° C. for 30 h, 1 N aqueous NaOH and dichloromethane were added. The aqueous layer was separated and the organic layer was dried over K2CO3, filtered and evaporated. Column chromatography (SiO2, 20% MeOH/AcOEt) gave 4-[N-{5-bromo-2-(dimethylamino)benzoyl)glycyl]aminomethyl-1-(4- chlorobenzyl)piperidine (Compound No. 1428) (60 mg, 82%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 523 (C24H30BrClF6N4O2).
Workup
- customThe aqueous layer was separated
- dry with materialthe organic layer was dried over K2CO3
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-2fb82e97a8494edd98eb0864d19ef4f0
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362177B1
Reaction notes
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