1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 72253692, compound

HRID 1429183Notes

Reaction equation

HRID 1429183 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:27][CH:26]3[CH:12]([C:13](=[O:33])[N:14]([CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]4[C:23]([C:29](O)=[O:30])([NH:24][C:25]3=[O:28])[CH2:22]4)[CH2:11]2)[CH:6]=[C:5]([O:34][CH3:35])[N:4]=1.[CH:36]1([S:39]([NH2:42])(=[O:41])=[O:40])[CH2:38][CH2:37]1.CCN=C=NCCCN(C)C.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:27][CH:26]3[CH:12]([C:13](=[O:33])[N:14]([CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]4[C:23]([C:29]([NH:42][S:39]([CH:36]5[CH2:38][CH2:37]5)(=[O:41])=[O:40])=[O:30])([NH:24][C:25]3=[O:28])[CH2:22]4)[CH2:11]2)[CH:6]=[C:5]([O:34][CH3:35])[N:4]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 68590387HCID 68590387, compound

Product 1

HCID 72253692HCID 72253692, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid 18g (1.2 g, 2 mmol) was reacted with cyclopropane sulfonamide (73 mg, 0.6 mmol), EDAC (115 mg, 0.6 mmol) and DBU (215 mg, 1.4 mmol) in dry DCM (3 ml) according to the procedure described in Example 13 step f. Purification by column chromatography on silica gel eluted with diethyl ether-ethyl acetate gave the title compound, (185 mg, 70%), (M+H)+592.

Workup

  1. customPurification by column chromatography on silica gel
  2. washeluted with diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-e5b4e9e32e7c47ac99b4c46bbce8025d
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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