Water → HCID 86690948, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:31][C@H:32]([OH:37])[C:33]([F:36])([F:35])[F:34])[C:10](=[O:30])[N:11]([CH2:13][C:14]3[CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=4[Cl:29])[CH:17]=[CH:18][C:19]=3[CH2:20][OH:21])[N:12]=2)=[CH:4][CH:3]=1.ClS([N:42]=[C:43]=[O:44])(=O)=O.O.C(=O)(O)[O-].[Na+]>ClCCl>[C:43](=[O:44])([O:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[Cl:29])=[CH:15][C:14]=1[CH2:13][N:11]1[C:10](=[O:30])[N:9]([CH2:31][C@H:32]([OH:37])[C:33]([F:34])([F:36])[F:35])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:12]1)[NH2:42]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
65 mg (0.11 mmol) of the compound from Example 137 were dissolved in 3 ml of dichloromethane, and the mixture was cooled to 0° C. 14 μl (0.16 mmol) of chlorosulfonyl isocyanate were added, and the mixture was stirred at RT for 18 h. 1.5 ml of water were then added, and the mixture was stirred at 60° C. for a further 18 h. For work-up, 3 ml of saturated aqueous sodium bicarbonate solution were added, and the mixture was extracted twice with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 30 mg (43% of theory) of the target compound.
Workup
- stirringthe mixture was stirred at 60° C. for a further 18 h
- extractionthe mixture was extracted twice with in each case 10 ml of ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified chromatographically [Method 19]
Sources & evidence
- ORD record
- ord-c20879505a2a43c6a6186cb5a9b10df8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187466B2
Reaction notes
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