Triethylamine → HCID 18005119, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.Cl[C:19](OC1C=CC=CC=1)=[O:20].C(N(CC)CC)C.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][C:45]=1[C:46]([F:49])([F:48])[F:47])[NH:42][CH2:41][CH2:40]2>ClCCl>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([NH:1][C:19]([N:42]4[C:43]5[C:39](=[CH:38][C:37]([O:36][CH3:35])=[C:45]([C:46]([F:49])([F:47])[F:48])[CH:44]=5)[CH2:40][CH2:41]4)=[O:20])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)=[CH:13][CH:14]=1Participants
6
Procedure
A mixture of aminoindole (D49, 0.46 g, 2.1 mmol), phenyl chloroformate (0.26 mL, 2.1 mmol) and triethylamine (0.29 mL, 2.1 mmol) in dichloromethane (5 mL) was stirred at room temperature for 1 h. The mixture was then diluted with dichloromethane, washed with water, dried and evaporated. The residue was dissolved in acetonitrile (10 mL). 5-Methoxy-6-trifluoromethylindoline (D11, 0.45 g, 2.1 mmol) and triethylamine (0.29 mL, 2.1 mmol) were added and the mixture was stirred for 3 h at room temperature. The reaction was worked up as for Example 71, and the solid obtained after trituration was recrystallised from dichloromethane/petrol to give the title compound (0.26 g, 27%), m.p. 215-8° C.
Workup
- washwashed with water
- customdried
- customevaporated
- dissolutionThe residue was dissolved in acetonitrile (10 mL)
- stirringthe mixture was stirred for 3 h at room temperature
- customthe solid obtained after trituration
- customwas recrystallised from dichloromethane/petrol
Sources & evidence
- ORD record
- ord-6e343e8cb45a4eb7b3a8c75c0eba74b8
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990133
Reaction notes
Loading…