2-Pentanamine → (2-{[5-(1-Methyl-butylcarbamoyl)-thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester

HRID 1790216Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]([C:23]([OH:25])=O)=[CH:20][CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:38][CH:39]([NH2:43])[CH2:40][CH2:41][CH3:42]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]([C:23](=[O:25])[NH:43][CH:39]([CH3:38])[CH2:40][CH2:41][CH3:42])=[CH:20][CH:19]=1)=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 4.4 g (12.1 mmol) 5-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid in 80 ml THF were added 2.2 g (13.6 mmol) carbonyldiimidazol. The reaction mixture was stirred at 45° C. for 1 h and then cooled to rt. After addition of 1.05 g (12 mmol) 2-pentylamine the reaction mixture was kept at rt for 12 h. The solvent was evaporated and the residue was dissolved in 150 ml CH2 Cl2. The solution was washed twice with 150 ml water each and dried over magnesium sulfate. The solvent was evaporated and the residue was washed with diethyl ether to yield (2-{[5-(1-methyl-butylcarbamoyl)-thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester as a white solid, mp. 183° C.

Workup

temperaturecooled to rt
waitwas kept at rt for 12 h
customThe solvent was evaporated
dissolutionthe residue was dissolved in 150 ml CH2 Cl2
washThe solution was washed twice with 150 ml water each and
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
washthe residue was washed with diethyl ether

Sources & evidence

ORD record: ord-a2cea9a32b0044a881f3c9217467f865
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071219B2

Reaction notes

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