Pyridine → Ammonia ethyl acetate

HRID 1633723Notes

Reaction equation

HRID 1633723 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[C:14]1[N:15]=[CH:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1.N1C=CC=C[CH:27]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[C:19]([O:21][CH2:22][CH3:25])(=[O:20])[CH3:27].[NH3:1].[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[C:3]2[C:8]=1[CH:7]([C:14]1[N:15]=[CH:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1)[CH2:6][CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 11290851Tert-butyl 4-(5-amino-8-methoxy-1,2,3,4-tetrahydro-1-naphthalenyl)-1h-imidazole-1-carboxylate

Product 2

HCID 11384659Tert-butyl 4-{8-methoxy-5-[(methylsulfonyl)amino]-1,2,3.4-tetrahydro-1-naphthalenyl}-1h-imidazole-1-carboxylateHCID 18464838Ammonia ethyl acetateYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 26D (0.50 g, 1.5 mmol) in dichloromethane (5 mL) was treated with pyridine (0.34 mL, 4.4 mmol), treated with methanesulfonyl chloride (0.17 mL, 2.2 mmol) and stirred for 1.5 hours. Purification of the mixture on silica gel eluting with ammonia-saturated dichloromethane and then with 10% ethyl acetate/ammonia-saturated dichloromethane provided the desired product which was dried under vacuum.

Workup

  1. customPurification of the mixture on silica gel eluting with ammonia-saturated dichloromethane

Sources & evidence

ORD record
ord-b56d9b5022c74636abaa45c45edb1dd8
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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