3-Pyridinemethanamine → HCID 56963557, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:60]1[CH:65]=[CH:64][CH:63]=[C:62]([CH2:66][NH2:67])[CH:61]=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:67][CH2:66][C:62]4[CH:61]=[N:60][CH:65]=[CH:64][CH:63]=4)=[O:23])=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])(=[O:10])=[O:9])=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
Benzoic acid 29 (150 mg, 0.34 mmol) was dissolved in anhydrous DMF (5 mL), DIEA (0.12 mL, 0.69 mmol) and HBTU (171 mg, 0.45 mmol) were successively added and the reaction mixture was stirred at 20° C. for 10 min. 3-Pyridinylmethanamine (0.14 mL, 1.4 mmol) was subsequently added and the reaction mixture was stirred at 20° C. for 1 h. The reaction mixture was diluted with EtOAc (150 mL), washed with H2O (3×50 mL), washed with brine (50 mL) and dried. The solvent evaporated and the residue was purified by column chromatography, eluting with a gradient (0-10%) MeOH/EtOAc, to afford benzamide 30 (170 mg, 94%) as a white solid: mp (EtOAc) 225-226° C.; spectroscopically identical to the sample prepare above.
Workup
- stirringthe reaction mixture was stirred at 20° C. for 1 h
- washwashed with H2O (3×50 mL)
- washwashed with brine (50 mL)
- customdried
- customThe solvent evaporated
- customthe residue was purified by column chromatography
- washeluting with a gradient (0-10%) MeOH/EtOAc
Sources & evidence
- ORD record
- ord-b9667c219a614d2a98fca624cef54b23
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296732B2
Reaction notes
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