Triethylamine → HCID 178432369, compound

HRID 1851291Notes

Reaction equation

HRID 1851291 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[CH2:31][CH2:30][CH:29]([C:32]2[N:33]=[C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[N:38]=3)[NH:35][N:36]=2)[CH2:28][CH2:27]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1.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[CH2:27][CH2:28][CH:29]([C:32]5[N:33]=[C:34]([C:37]6[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:45])([F:46])[F:44])[N:38]=6)[NH:35][N:36]=5)[CH2:30][CH2:31]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

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehydeHCID 178478964HCID 178478964, compound

Product 1

HCID 178432369HCID 178432369, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 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) and 2-(5-piperidin-4-yl-2H-[1,2,4]triazol-3-yl)-6-trifluoromethyl-pyridine hydrochloride salt (662 mg, 1.43 mmol) in NMP (8.1 mL) was treated with Et3N (0.32 mL), followed by AcOH (98 μL) and the mixture was stirred overnight at rt. NaBH(OAc)3 (222 mg) was added and the mixture stirred for 3 hours. The mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution, the organic phase washed with brine and concentrated in vacuo. The crude product was purified by preparative HPLC to give the title compound.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. customThe mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  3. washthe organic phase washed with brine
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-05fbb87f66f9493b8facc9b334c827c1
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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