2-Pyridinemethanamine → N-(pyridin-2-ylmethyl)-4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzamide
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23]6[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=6)[CH:21]=[N:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][NH2:39].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CO>[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][NH:39][C:27](=[O:29])[C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:21]=[N:22][C:17]3[N:18]([C:14]([C:11]4([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[N:1]=[CH:2][CH:3]=[CH:4]6)[CH2:12][CH2:13]4)=[N:15][N:16]=3)[N:19]=2)=[CH:31][CH:30]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoic acid (10 mg, 0.00002 mol), 2-pyridinemethanamine (2.9 mg, 0.000027 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (12 mg, 0.000027 mol), N,N-diisopropylethylamine (11 μL, 0.000061 mol) in DMF (0.4 mL) was stirred at RT for 2 h. The mixture was diluted with methanol and purified by RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=499.1.
Workup
- custompurified by RP-HPLC (pH=10)
Sources & evidence
- ORD record
- ord-39e8b2708f0d4051a5bd31c936f1149d
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143251B2
Reaction notes
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