Triethylamine → HCID 178424645, compound

HRID 1851287Notes

Reaction equation

HRID 1851287 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:6]=2)[CH2:2]1.C([N:19]([CH2:22]C)[CH2:20][CH3:21])C.C1([C:27]2[CH:34]=[C:33]([C:35]3[C:40]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[CH:39][N:38]4[N:48]=CN=C4[N:36]=3)[CH:32]=[CH:31][C:28]=2[CH:29]=O)CC1.[BH-](OC(C)=O)(OC(C)=O)O[C:53]([CH3:55])=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[CH:21]1([C:20]2[N:19]=[C:22]3[N:36]=[C:35]([C:33]4[CH:34]=[CH:27][C:28]([CH2:29][N:1]5[CH2:4][CH:3]([C:5]6[N:6]=[C:7]([C:10]7[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=7)[NH:8][N:9]=6)[CH2:2]5)=[CH:31][CH:32]=4)[C:40]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[CH:39][N:38]3[N:48]=2)[CH2:55][CH2:53]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 867030522-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

Product 1

HCID 178424645HCID 178424645, compoundYield 58.3%

Reagents, catalysts & solvents 2

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

Procedure

164.5 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 4.2 mL NMP. After addition of 0.16 mL triethylamine the reaction mixture is stirred for one hour. 350 mg 2-cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde (50% pure) and 0.05 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 113.8 mg (0.54 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. After the usual work-up and chromatography 167 mg (58.3%) of the desired product are obtained.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours

Sources & evidence

ORD record
ord-f65bfb8561a444c698cfed32a32afd99
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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