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Sodium Bicarbonate → HCID 178498892, compound

HRID 1851280
Notes
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Reaction equation

HRID 1851280 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.[CH3:16][O:17][C:18]([C:20]1[CH:21]=[N:22][N:23]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[C:26]([C:37]3[CH:42]=[CH:41][C:40]([CH:43]=O)=[CH:39][CH:38]=3)=[N:25][C:24]=12)=[O:19].[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>[CH3:16][O:17][C:18]([C:20]1[CH:21]=[N:22][N:23]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])[C:26]([C:37]3[CH:42]=[CH:41][C:40]([CH2:43][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:39][CH:38]=3)=[N:25][C:24]=12)=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030506-(2,4-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester

Product 1

HCID 178498892HCID 178498892, compound

Reagents, catalysts & solvents

3
HCID 176Acetic AcidSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

49.8 mg (0.18 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 1.4 mL NMP. After addition of 0.06 mL triethylamine the reaction mixture is stirred for one hour. 65 mg (0.17 mmol) 6-(2,4-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester in 1.5 mL NMP and 0.02 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 38.5 mg (0.18 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) 23.4 mg (23%) 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
  3. stirringstirred vigorously for one hour
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-77f6a261c9da4f28b3d76bb816988f38
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes