Triethylamine → HCID 178432370, compound

HRID 1851275Notes

Reaction equation

HRID 1851275 reaction equation
[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.Cl.[NH:26]1[CH2:30][CH2:29][CH:28]([C:31]2[N:32]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[NH:34][N:35]=2)[CH2:27]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.O.CC(O)=O>[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:26]4[CH2:30][CH2:29][CH:28]([C:31]5[N:32]=[C:33]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[NH:34][N:35]=5)[CH2:27]4)=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehydeHCID 178477977HCID 178477977, compound

Product 1

HCID 178432370HCID 178432370, compoundYield 10.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (300 mg, 0.95 mmol), 2-(5-pyrrolidin-3-yl-2H-[1,2,4]triazol-3-yl)-pyridine hydrochloride salt (358 mg), triethylamine (0.32 mL) and AcOH (0.098 mL) in NMP (8.1 mL) was stirred overnight at room temperature. Sodium triacetoxyborohydride (222 mg) was added and the mixture stirred for 4 h. The mixture was diluted with water, filtered and the filtrate concentrated in vacuo. The residue was co-distilled with toluene and to give the crude product which was purified by preparative HPLC to give the title compound (50 mg).

Workup

  1. stirringthe mixture stirred for 4 h
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give the crude product which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-6770911559b84ce7ba4352d0e884f4c7
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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