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Diisopropylethylamine → HCID 23121832, compound

HRID 1713549
Notes
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Reaction equation

HRID 1713549 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].[C:40]1([C:46]2([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH:50]3[CH2:51][NH:52][CH2:53][CH2:54][N:49]3[C:48](=[O:55])[O:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1.C(OCC)(=O)C>[O:55]=[C:48]1[N:49]2[CH2:54][CH2:53][N:52]([C:28]([NH:1][C:2]3[C:10]4[N:9]=[CH:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]=4[CH:5]=[CH:4][CH:3]=3)=[O:29])[CH2:51][CH:50]2[C:46]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[O:47]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 18355224tert-butyl 4-amino-1H-benzo[d]imidazole-1-carboxylateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121832HCID 23121832, compoundYield 66.2%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-amino-1H-benzimidazole-1-carboxylate (0.12 g, 0.50 mmol) in tetrahydrofuran (10 ml) were added diisopropylethylamine (90 μL, 0.50 mmol) and 4-nitrophenyl chloroformate (0.11 g, 0.50 mmol), and the mixture was stirred at room temperature for 4 hours. Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (88 mg, 0.30 mmol) and diisopropylethylamine (90 μL, 0.50 mmol) were sequentially added thereto, and the mixture was stirred at room temperature overnight. To the reaction solution were added ethyl acetate (50 mL) and a 0.5 M aqueous sodium hydrogen carbonate solution (50 mL), and the obtained crystals were collected by filtration. The crude crystals were sequentially washed with a 0.5 M aqueous sodium hydrogen carbonate solution, water and ethyl acetate to obtain the title compound (0.11 g, yield 65%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationa 0.5 M aqueous sodium hydrogen carbonate solution (50 mL), and the obtained crystals were collected by filtration
  3. washThe crude crystals were sequentially washed with a 0.5 M aqueous sodium hydrogen carbonate solution, water and ethyl acetate

Sources & evidence

ORD record
ord-e96e984172474199a9b694d2934f0013
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795267B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes