Cyanamide → N-cyano-2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:26])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][N:15]([C:17]3[CH:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[CH:19][N:18]=3)[CH:16]=2)=[CH:4][CH:3]=1.[N:27]#[C:28][NH2:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:28]([NH:29][C:23]([C:21]1[CH:20]=[CH:19][N:18]=[C:17]([N:15]2[CH:16]=[C:12]([CH2:11][CH2:10][N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH3:26])[CH:13]=[N:14]2)[CH:22]=1)=[O:25])#[N:27]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxylic acid (70 mg, 0.2 mmol), cyanamide (17 mg, 0.4 mmol), HATU (113 mg, 0.3 mmol) and DIEA (59 mg, 0.6 mmol) in DMF (3 mL) was stirred at room temperature for 3 hours. The mixture was concentrated and purified by prep-HPLC to give the compound (15 mg, 20%). 1H NMR (400 MHz, DMSO-d6): 2.67-2.74 (3H, m), 2.94-2.98 (2H, m), 3.28 (1H, m), 3.43-3.45 (1H, m), 4.26-4.30 (1H, m), 4.44-4.48 (1H, m), 7.31-7.36 (2H, m), 7.59-7.61 (2H, m), 7.70-7.71 (1H, m), 7.76 (1H, s), 8.31 (1H, s), 8.42 (1H, d, J=5.2 Hz), 8.58 (1H, s), 9.56 (1H, br). [M+H] Calc'd for C20H19FN6O, 379. Found, 379.
Workup
- concentrationThe mixture was concentrated
- custompurified by prep-HPLC
Sources & evidence
- ORD record
- ord-1a7f17392fd34eb991bfdf3b65e8a2de
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09107916B2
Reaction notes
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