Diisopropylethylamine → HCID 178430833, 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]([F:12])[CH:7]=1)#[N:2].ClC1C=C(NC(=NC#N)OC2C=CC=CC=2)C=CC=1.[CH3:39][C:40]1[C:48]2[C:47]([N:49]3[CH2:54][CH2:53][NH:52][C@@H:51]([CH3:55])[CH2:50]3)=[N:46][CH:45]=[N:44][C:43]=2[NH:42][CH:41]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]([N:3]=[C:4]([N:52]1[CH2:53][CH2:54][N:49]([C:47]2[C:48]3[C:40]([CH3:39])=[CH:41][NH:42][C:43]=3[N:44]=[CH:45][N:46]=2)[CH2:50][C@@H:51]1[CH3:55])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1)#[N:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
Phenyl N′-cyano-N-(3-fluorophenyl)carbamimidate, prepared analogously to phenyl N-3-chlorophenyl-N′-cyanocarbamimidate from Example 6, step A, (0.55 g, 2.2 mmol), (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine, from example 1, step B, (0.50 g, 2.2 mmol), and N,N-diisopropylethylamine (1 ml) were added to acetonitrile (10 ml). The mixture was heated at 85° C. in a sealed pressure tube for 4 hours. The solvent was evaporated, and the residue was purified prep HPLC (Sunfire C18 30×250 mm column. 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min) to give (S)—N′-cyano-N-(3-fluorophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide (0.23 g, 0.58 mmol, 27%).
Workup
- customThe solvent was evaporated
- customthe residue was purified prep HPLC (Sunfire C18 30×250 mm column. 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min)
Sources & evidence
- ORD record
- ord-f14392d52b36482b827fee5f3eec4aeb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507672B2
Reaction notes
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