Sodium Bicarbonate → HCID 178424648, compound

HRID 1851276Notes

Reaction equation

HRID 1851276 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.[CH3:17][C:18]1[N:22]2[CH:23]=[C:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:25]([C:27]3[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=3)=[N:26][C:21]2=[N:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.C(N(CC)CC)C>[CH3:17][C:18]1[N:22]2[CH:23]=[C:24]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:25]([C:27]3[CH:34]=[CH:33][C:30]([CH2:31][N:1]4[CH2:4][CH:3]([C:5]5[N:6]=[C:7]([C:10]6[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=6)[NH:8][N:9]=5)[CH2:2]4)=[CH:29][CH:28]=3)=[N:26][C:21]2=[N:20][CH:19]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 867030494-(3-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 178424648HCID 178424648, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

168 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (intermediate example 44.1; 60% pure) are dissolved in 2.8 ml NMP. After addition of 0.1 ml triethylamine the reaction mixture is stirred for one hour. 100 mg (0.32 mmol) 4-(3-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde (intermediate example 12.0) and 0.03 mL acetic acid are added and the reaction mixture is stirred overnight at room temperature. 74.4 mg (0.35 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is treated with saturated NaHCO3 and the precipitate filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 36.6 mg (21%) 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 20 hours
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d78cb106d4ef4218b35f2411feb3e1d1
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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