Dimethylformamide → N3-[amino(imino)methyl]-N3-methyl-N-[4-(triphenylphosphonio)butyl]-beta-alaninamide bromide
Reaction equation
CNCCC(NC[CH2:9][CH2:10][CH2:11][P+:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[Br-:31].Cl.[N:33]1([C:38](=[NH:40])[NH2:39])[CH:37]=[CH:36]C=N1.[CH:41](N(CC)C(C)C)(C)C.[CH3:50][N:51](C)[CH:52]=[O:53]>>[NH2:39][C:38](=[NH:40])[N:33]([CH3:41])[CH2:37][CH2:36][C:52]([NH:51][CH2:50][CH2:9][CH2:10][CH2:11][P+:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:53].[Br-:31]Participants
5
Reactant 4
Product 1
Procedure
N3-methyl-N-[4-(triphenylphosphonio)butyl]-β-alaninamide bromide (980 mg, 2.0 mmol) was dissolved in N,N-dimethylformamide (2 mL). The resultant solution was treated with 1H-pyrazole-1-carboximidamide hydrochloride (315 mg, 2.15 mmol) and N,N-diisopropylethylamine (0.39 mL, 2.26 mmol). The reaction was stirred overnight at room temperature. More 1H-pyrazole-1-carboximidamide hydrochloride and N,N-diisopropylethylamine can be added to effect further conversion. The reaction mixture in N,N-dimethylformamide was used without work-up in the next step.
Sources & evidence
- ORD record
- ord-fb4e85a7232447ad8e7d394428661f39
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434753B2
Reaction notes
Loading…