Sodium Bicarbonate → HCID 178432367, compound

HRID 1851277Notes

Reaction equation

HRID 1851277 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]=[CH:12][N:11]=3)[N:6]=2)[CH2:2]1.[Br:16][C:17]1[N:21]2[CH:22]=[C:23]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:24]([C:26]3[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=3)=[N:25][C:20]2=[N:19][C:18]=1[CH3:40].[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>[Br:16][C:17]1[N:21]2[CH:22]=[C:23]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:24]([C:26]3[CH:27]=[CH:28][C:29]([CH2:30][N:1]4[CH2:4][CH:3]([C:5]5[N:6]=[C:7]([C:10]6[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=6)[NH:8][N:9]=5)[CH2:2]4)=[CH:32][CH:33]=3)=[N:25][C:20]2=[N:19][C:18]=1[CH3:40]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030354-(3-Bromo-2-methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 178432367HCID 178432367, compound

Reagents, catalysts & solvents 3

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

Procedure

147.6 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl (intermediate example 44.0) are dissolved in 4.3 ml NMP. After addition of 0.16 ml triethylamine the reaction mixture is stirred for one hour. 192 mg (0.49 mmol) 4-(3-Bromo-2-methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde and 0.05 mL acetic acid are added and the reaction mixture is stirred for 23 hours at room temperature. 114.1 mg (0.54 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for three days. The reaction mixture is treated with 30 mL saturated NaHCO3 and stirred for 45 minutes. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 3.5 mg (1.2%) of the desired product are obtained.

Workup

  1. stirringthe reaction mixture is stirred for 23 hours at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for three days
  3. stirringstirred for 45 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5c4a507dbfbb4a66a5732d05e3c08d07
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…