1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,3-Dichloro-N-{(1S,2S)-1-[(methylsulfonyl)amino]-2,3-dihydro-1H-inden-2-yl}-4H-thieno[3,2-b]pyrrole-5-carboxamide

HRID 1244711Notes

Reaction equation

HRID 1244711 reaction equation
[C:1]([C:4]1[NH:8][C:7]2[C:9]([Cl:13])=[C:10]([Cl:12])[S:11][C:6]=2[CH:5]=1)([OH:3])=O.[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>[Cl:12][C:10]1[S:11][C:6]2[CH:5]=[C:4]([C:1]([NH:14][C@H:15]3[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C@@H:16]3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:3])[NH:8][C:7]=2[C:9]=1[Cl:13]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 100143182,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acidHCID 58742479N-[(1S,2S)-2-amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamide

Product 1

HCID 102168792,3-Dichloro-N-{(1S,2S)-1-[(methylsulfonyl)amino]-2,3-dihydro-1H-inden-2-yl}-4H-thieno[3,2-b]pyrrole-5-carboxamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 4, 236 mg, 1.0 mmol), N-[(1S,2S)-2-amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamide (226 mg, 1.0 mmol), DIPEA (174 μL, 1.0 mmol) and HOBT (135 mg, 1.0 mmol) were dissolved in DCM (10 mL) and stirred for approximately 5 mins. EDCI (240 mg, 1.25 mmol) was added and the reaction stirred for 20 hours. The volatiles were removed by evaporation, EtOAc (25 mL) added, the mixture washed with water (2×10 mL) and brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (430 mg, 97%) as a foam.

Workup

  1. stirringthe reaction stirred for 20 hours
  2. customThe volatiles were removed by evaporation, EtOAc (25 mL)
  3. additionadded
  4. washthe mixture washed with water (2×10 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customThe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-05417cda731b4ec187b4f0b3239abad6
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

Loading…