Furfurylamine → HCID 136347300, compound
Reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([NH2:14])[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.[NH2:15][C:16]1[CH:44]=[CH:43][C:19]2[NH:20][C:21]([C:26]3[C:27](=[O:42])[N:28]([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:29]4[C:34]([C:35]=3[OH:36])=[CH:33][CH:32]=[CH:31][N:30]=4)=[N:22][S:23](=[O:25])(=[O:24])[C:18]=2[CH:17]=1.C(N(CC)CC)C>ClCCl>[O:13]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:8][NH:14][C:6]([NH:5][S:2](=[O:4])(=[O:3])[NH:15][C:16]1[CH:44]=[CH:43][C:19]2[NH:20][C:21]([C:26]3[C:27](=[O:42])[N:28]([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:29]4[C:34]([C:35]=3[OH:36])=[CH:33][CH:32]=[CH:31][N:30]=4)=[N:22][S:23](=[O:25])(=[O:24])[C:18]=2[CH:17]=1)=[O:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of chlorosulfonyl isocyanate (4.9 μL, 0.0562 mmol) in dichloromethane (2 mL) was treated dropwise with furfurylamine (5 μL, 0.0562 mmol) at 25° C., stirred at 25° C. for 30 min, treated with a solution of product of Example 205 (20 mg, 0.0468 mmol) and triethylamine (26 μL, 0.187 mmol) in dichloromethane (2 mL) and stirred for 24 hours at 25° C. The reaction mixture was partitioned between dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL). The resulting organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the title compound (15%). MS m/z 630 (M+H)+.
Workup
- stirringstirred for 24 hours at 25° C
- customThe reaction mixture was partitioned between dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL)
- customThe resulting organic layer was separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-20689dc2cbce4b728e236f4d70fe2b51
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902203B2
Reaction notes
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