Formic Acid → HCID 58515972, compound

HRID 717833Notes

Reaction equation

HRID 717833 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.Cl.[NH2:12][CH2:13][C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[C:17]([C:33]([O:35][CH3:36])=[O:34])=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([NH:12][CH2:13][C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[C:17]([C:33]([O:35][CH3:36])=[O:34])=[CH:16][CH:15]=1)=[O:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 66993102HCID 66993102, compound

Product 1

HCID 58515972HCID 58515972, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formic acid (2.2 mL, 58 mmol) and acetic anhydride (5.2 mL, 58 mmol) were stirred at room temperature for 1 hour. The mixture was added dropwise to a solution of tert-butyl 4-[6-(aminomethyl)-3-(methoxycarbonyl)pyridin-2-yl]piperazine-1-carboxylate hydrochloride (4.9 g, 13 mmol) in methylene chloride (90 mL) at 0° C. and stirred for 48 hours. Evaporation gave the crude material which was treated with sodium bicarbonate and extracted with methylene chloride to give the desired compound (4.9 g, 100%). LCMS calculated for C18H27N4O5 (M+H)+: m/z=379.2. found: 378.9.

Workup

  1. customEvaporation
  2. customgave the crude material which
  3. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-2cd992226efb46fabbb64fc1c12c9bbc
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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