Diethylethanolamine → 2-(diethylamino)ethyl N-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]carbamate

HRID 991017Notes

Reaction equation

[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].[H-].[Na+].[N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:22]=3[NH:23][N:24]=2)=[CH:16][CH:15]=1)=[C:12]=[O:13]>C1COCC1>[NH:23]1[C:22]2[C:25]3[C:30]([CH2:31][C:21]=2[C:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:11][C:12](=[O:13])[O:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[CH:19][CH:18]=2)=[N:24]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of N,N-diethyl ethanol amine (0.368 mL, 2.75 mmol) in THF (5 mL) was added NaH (60% in mineral oil, 113 mg, 2.75 mmol). The reaction mixture was stirred at about 20° C., for about 1 hour then solid 3-(4-isocyanatophenyl)-1,4-dihydroindeno[1,2-c]pyrazole, 2 (58 mg, 0.22 mmol) was added. The reaction mixture was heated to about 45° C., for about 3 hours. The reaction mixture was quenched by addition of H2O and the product was extracted into EtOAc. The crude material was purified by flash chromatography on SiO2 (MeOH/CH2Cl2, 10/90) to give 51 mg (62%) of pure product. LC/MS 391 (M+1); LC retention time 2.68 minutes.

Workup

temperatureThe reaction mixture was heated to about 45° C., for about 3 hours
customThe reaction mixture was quenched by addition of H2O
extractionthe product was extracted into EtOAc
customThe crude material was purified by flash chromatography on SiO2 (MeOH/CH2Cl2, 10/90)

Sources & evidence

ORD record: ord-95f788dedb78401cbd8174b990e15182
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462036B1

Reaction notes

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