1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24886043, compound

HRID 722258Notes

Reaction equation

HRID 722258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[NH2:14][C@@H:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:16]1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:14][C@@H:15]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@H:16]1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:13])=[CH:5]2

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 67220650N-[(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamide

Product 1

HCID 24886043HCID 24886043, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-1H-indol-2-carboxylic acid (196 mg, 1.0 mmol), N-[(1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamide (Method 2; 226 mg, 1.0 mmol), DIPEA (0.17 ml, 1.0 mmol), and HOBT (130 mg, 1.0 mmol) was stirred in DCM (10 ml) for one minute. EDCI (240 mg, 1.25 mmol) was added and the mixture stirred at room temperature for 20 hours. The mixture was diluted with EtOAc, washed with water (2×25 ml), dried over magnesium sulphate and evaporated to give the title compound (320 mg, 79%) as a foam.

Workup

  1. washwashed with water (2×25 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-3fd40ee2e5b446b29136256b57d3538d
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

Loading…