6-(Benzyloxy)pyridine-3-carboxylic acid → 3-Pyridinecarboxamide, N-(2-amino-2-oxoethyl)-6-(phenylmethoxy)-

HRID 433211Notes

Reaction equation

HRID 433211 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:19][CH2:20][C:21]([NH2:23])=[O:22].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:19][CH2:20][C:21](=[O:22])[NH2:23])=[O:15])=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2772386-(Benzyloxy)pyridine-3-carboxylic acidHCID 2723639Glycinamide hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 103083013-Pyridinecarboxamide, N-(2-amino-2-oxoethyl)-6-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-benzyloxy-nicotinic acid (500 mg, 2.18 mmol), glycinamide HCI (265 mg, 2.4 mmol), 4-dimethylamino pyridine (133 mg; 1.09 mmol), N-(3-dimethylamino-propyl)-N′-ethylcarbodiimide HCl (460 mg; 2.4 mmol) and methylene chloride (10 ml) was stirred at 0° C. for 1 h then at r.t. overnight. The precipitate was filtered off and washed with methylene chloride and water. The title compound was obtained as a white solid (328 mg; 53%). MS: m/e=286.2 (M+H+).

Workup

  1. customat r.t.
  2. customovernight
  3. filtrationThe precipitate was filtered off
  4. washwashed with methylene chloride and water

Sources & evidence

ORD record
ord-dbf8356fcb4e479e89232faa8c861e2d
Source dataset
uspto-grants-2003_12
Patent number
US06667327B2

Reaction notes

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