Triethylamine → HCID 178430829, compound
Reaction equation
[C:1]([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)#[N:2].BrC1C=C(NC(=NC#N)[O-])C=CC=1.[CH3:36][C:37]1[C:45]2[C:44]([N:46]3[CH2:51][CH2:50][NH:49][C@@H:48]([CH3:52])[CH2:47]3)=[N:43][CH:42]=[N:41][C:40]=2[NH:39][CH:38]=1.C(N(CC)CC)C>C(O)(C)C>[C:1]([N:3]=[C:4]([N:49]1[CH2:50][CH2:51][N:46]([C:44]2[C:45]3[C:37]([CH3:36])=[CH:38][NH:39][C:40]=3[N:41]=[CH:42][N:43]=2)[CH2:47][C@@H:48]1[CH3:52])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)#[N:2]Participants
6
Conditions
- Temperature
- 140 °C
Procedure
Phenyl N′-cyano-N-(3-(trifluoromethyl)phenyl)carbamimidate, prepared analogously to N-3-bromophenyl-N′-cyanocarbamimidate from Example 5, step A (36 mg, 0.12 mmol), (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine, from Example 1, step B, (35 mg, 0.15 mmol), and triethylamine (0.05 ml, 0.36 mmol) were combined in isopropanol in a microwave vessel. The reaction was heated at 140° C. for 30 min. under microwave conditions. The solvent was evaporated, and the residue was washed with CH2Cl2 (3×10 ml). The crude product was purified by Prep-HPLC to afford (S)—N′-cyano-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-(3-(trifluoromethyl)phenyl)-piperazine-1-carboximidamide as white solid.
Workup
- customThe solvent was evaporated
- washthe residue was washed with CH2Cl2 (3×10 ml)
- customThe crude product was purified by Prep-HPLC
Sources & evidence
- ORD record
- ord-c797dc14195d49fb8f07366ff2eca363
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507672B2
Reaction notes
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