tert-butyl N-(4-aminobutyl)carbamate → [4-(1-Pyrazin-2-yl-ethylamino)-butyl]-carbamic acid tert-butyl ester

HRID 251015

Reaction equation

HRID 251015 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[C:14]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)(=O)[CH3:15].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH:14]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)[CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 30914AcetylpyrazineHCID 4311764Sodium borohydride

Product 1

HCID 67272616[4-(1-Pyrazin-2-yl-ethylamino)-butyl]-carbamic acid tert-butyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure B: Reaction of (4-amino-butyl)-carbamic acid tert-butyl ester and 2-acetyl pyrazine in MeOH with NaBH4 gave [4-(1-pyrazin-2-yl-ethylamino)-butyl]-carbamic acid tert-butyl ester (294 mg, 91%) as a colorless oil. 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.50-1.57 (m, 4H), 1.59 (d, 3H, J=6.6 Hz), 2.38-2.43 (m, 1H), 2.51-2.59 (m, 1H), 3.08-3.14 (m, 2H), 3.08 (m, 2H), 3.91 (d, 1H, J=6.7 Hz), 4.72 (bs, 1H), 8.45 (d, 1H, J=2.5 Hz), 8.53 (d, 1H, J=2.6 Hz), 8.60 (s, 1H).

Sources & evidence

ORD record
ord-4d6ae50c524e4a61ad21449c548a6123
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Linked notes

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