Sulfuric acid, dipropyl ester → (S)-8-[(1-tert-butoxycarbony-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

HRID 1970027Notes

Reaction equation

HRID 1970027 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].[C:22]([O:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][NH:35][CH:36]1[CH2:38][CH2:37]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(OS(OCCC)(=O)=O)CC>>[C:22]([O:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][N:35]([CH:36]1[CH2:37][CH2:38]1)[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[CH:18][C:8]=3[C:7]=2[CH:6]=1)(=[O:3])=[O:4])=[O:28])([CH3:25])([CH3:23])[CH3:24].[CH2:18]([C:19]([O-:21])=[O:20])[CH2:8][CH3:7]

Participants

4

Reactant 3

HCID 69015Sulfuric acid, dipropyl esterHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acidHCID 66569218(S)-2-Cyclopropylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86627532(S)-8-[(1-tert-butoxycarbony-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

Procedure

(S)-8-[(1-tert-butoxycarbony-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate is prepared according to synthesis 111, from 326 mg (1 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid and 288 mg (1.2 mmol) of (S)-1-tert-butoxycarbonyl-2-cyclopropylaminomethyl-pyrrolidine to give, after esterification according to general method C (using di-n-propylsulfate as the dialkylsulfate) and purification by chromatography on silica (eluent dichloromethane/methanol 99/1 then 95/5), 99 mg (17% in two stages) of (S)-8-[(1-tert-butoxycarbonyl-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a white solid.

Workup

  1. customto give
  2. custompurification by chromatography on silica (eluent dichloromethane/methanol 99/1

Sources & evidence

ORD record
ord-7e5ace70b1614b70be0996cd24e7e9ec
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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