Acetic Acid → HCID 57845321, compound

HRID 734863Notes

Reaction equation

HRID 734863 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([CH2:40][CH2:41][CH:42]=O)=[N:38][CH:39]=3)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.[CH3:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([CH2:40][CH2:41][CH2:42][N:48]4[CH2:49][CH2:50][CH:45]([CH3:44])[CH2:46][CH2:47]4)=[N:38][CH:39]=3)=[N:30][CH:31]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 693814-MethylpiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86076940HCID 86076940, compound

Product 1

HCID 57845321HCID 57845321, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

74 mg (0.35 mmol) of sodium triacetoxyborohydride and 41 μL (0.73 mmol) of HOAc were added to a solution of 100 mg (0.288 mmol) of 3-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}propionaldehyde and 34 μL (0.288 mmol) of 4-methylpiperidine in 6 mL of THF and the mixture was stirred for 16 hours at RT. Saturated aqueous sodium bicarbonate solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. Yield: 44 mg (35% of theoretical); C27H28ClN3 (M=429.984); calc.: molpeak (M+H)+: 430/432 (Cl); found: molpeak (M+H)+: 430/432 (Cl); HPLC-MS: 7.65 minutes (method A).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated down in vacuo
  4. custom7.65 minutes (method A)

Sources & evidence

ORD record
ord-d742059491aa4de982b7fd66b55b4808
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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