2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane → butyl 2-[[(2R)-2-[2-[[4-(N-benzoylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

HRID 1357802

Reaction equation

HRID 1357802 reaction equation
[C:1]1([C:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]3[N:24]([CH3:25])[C:23]4[CH:26]=[CH:27][C:28]([C@@:30]([NH:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])([C:32]([N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)=[O:33])[CH3:31])=[CH:29][C:22]=4[N:21]=3)=[CH:14][CH:13]=2)=[NH:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCN2CCN(C)P1N(C)[CH2:50][CH2:51]2>C(O)CCC>[C:1]1([C:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]3[N:24]([CH3:25])[C:23]4[CH:26]=[CH:27][C:28]([C@@:30]([NH:39][CH2:40][C:41]([O:43][CH2:44][CH2:45][CH2:50][CH3:51])=[O:42])([C:32]([N:34]5[CH2:35][CH2:36][CH2:37][CH2:38]5)=[O:33])[CH3:31])=[CH:29][C:22]=4[N:21]=3)=[CH:14][CH:13]=2)=[NH:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 41867232,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 145816407ethyl 2-[[(2R)-2-[2-[[4-(N-benzoylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

Product 1

HCID 145816429butyl 2-[[(2R)-2-[2-[[4-(N-benzoylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 0.3 g (0.53 mmol) of (R)-2-[4-(N-phenylcarbonylamidino)-phenylaminomethyl]-1-methyl-5-[1-(ethoxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole in 5 ml of n-butanol is mixed with 0.1 g (0.46 mmol) of 2,8,9-trimethyl-1-phospha-2,5,8,9-tetraazabicyclo[3.3.3]undecane and stirred for 1 hour at room temperature. The reaction mixture is purified on silica gel, eluting with ethyl acetate/ethanol/conc. ammonia (50:0.95:0.05 and 20:0.95:0.05). The uniform fractions are combined and concentrated by evaporation.

Workup

  1. customThe reaction mixture is purified on silica gel
  2. washeluting with ethyl acetate/ethanol/conc
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-22877f2c8a55406ba1534bbc6b37e6b7
Source dataset
uspto-grants-2003_07
Patent number
US06593355B2

Linked notes

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