Sodium Bicarbonate → HCID 178505523, compound

HRID 1851281Notes

Reaction equation

HRID 1851281 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.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([C:32]3[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=3)=[N:25][C:26]3[N:27]([CH:29]=[CH:30][N:31]=3)[CH:28]=2)=[CH:19][CH:18]=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>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24]([C:32]3[CH:39]=[CH:38][C:35]([CH2:36][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:34][CH:33]=3)=[N:25][C:26]3[N:27]([CH:29]=[CH:30][N:31]=3)[CH:28]=2)=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030204-[6-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl]-benzaldehyde

Product 1

HCID 178505523HCID 178505523, compound

Reagents, catalysts & solvents 3

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

Procedure

95 mg (0.35 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 2.7 mL NMP. After addition of 0.1 mL triethylamine the reaction mixture is stirred for one hour. 100 mg (0.32 mmol) 4-[6-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl]-benzaldehyde and 0.03 mL acetic acid are added. The reaction mixture is stirred for three days at room temperature. 73 mg (0.35 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is treated with saturated NaHCO3 and stirred vigorously for one hour. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 90 mg (54%) of the desired product are obtained.

Workup

  1. stirringThe reaction mixture is stirred for three days at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. stirringstirred vigorously for one hour
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7e1beb36d9af4b558861a866a169d5e5
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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