Diisopropylethylamine → 4-[[(7aR)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile

HRID 413346Notes

Reaction equation

HRID 413346 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[C:5]([O:19][Si](C(C)(C)C)(C)C)[CH:4]=1)#[N:2].C(N(C(C)C)CC)(C)C.Cl.C[O:38][C:39](=O)[C@H:40]1[CH2:44][CH2:43][CH2:42][NH:41]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CO>[Br:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:11]1[C:39](=[O:38])[C@H:40]2[CH2:44][CH2:43][CH2:42][N:41]2[C:10]1=[N:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[OH:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 12043083N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimideHCID 44629857Methyl D-prolinate hydrochloride

Product 1

HCID 98878184-[[(7aR)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrileYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (107 mg, 0.25 mmol), diisopropylethylamine (71 μL, 0.55 mmol), D-proline methyl ester hydro chloride (46 mg, 0.28 mmol) and TBAF (0.30 mL, 0.30 mmol) in THF (2.5 mL) and methanol (0.1 mL) to give 80 mg (78%) of 4-[[(7aR)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. MS(EI) m/e 411 (100(M+)).

Sources & evidence

ORD record
ord-d32aac2fbca5403eade4b7c302b297dc
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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