Triethylamine → HCID 178424651, compound

HRID 1851283Notes

Reaction equation

HRID 1851283 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(CC)CC)C.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[C:32]1[C:33]([C:42]2[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=2)=[N:34][C:35]2[N:36]([N:38]=[C:39]([CH3:41])[N:40]=2)[CH:37]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[C:32]1[C:33]([C:42]2[CH:43]=[CH:44][C:45]([CH2:46][N:1]3[CH2:4][CH:3]([C:5]4[N:6]=[C:7]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=5)[NH:8][N:9]=4)[CH2:2]3)=[CH:48][CH:49]=2)=[N:34][C:35]2[N:36]([N:38]=[C:39]([CH3:41])[N:40]=2)[CH:37]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 867030514-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

Product 1

HCID 178424651HCID 178424651, compound

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 4.8 mL NMP. After addition of 0.2 mL triethylamine the reaction mixture is stirred for one hour. 200 mg (0.57 mmol) 4-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.06 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 207.4 mg (0.98 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for another night. The reaction mixture is poured on saturated NaHCO3/ice water. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 92.2 mg (27.9%) 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 another night
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ba8518b055fb4d2d8f5039e5b769382f
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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