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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl((1r,2r)-2-{[(2,3-dichloro-4h-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1h-inden-1-yl)methylcarbamate

HRID 1244729
Notes
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Reaction equation

HRID 1244729 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.[C:14]([O:18][C:19](=[O:32])[NH:20][CH2:21][C@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][C@H:23]1[NH2:31])([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:14]([O:18][C:19](=[O:32])[NH:20][CH2:21][C@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][C@H:23]1[NH:31][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)=[O:3])([CH3:17])([CH3:15])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 86607601tert-butyl [(1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl]methylcarbamate

Product 1

HCID 131725988
Tert-butyl((1r,2r)-2-{[(2,3-dichloro-4h-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1h-inden-1-yl)methylcarbamate
Yield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 4, 472 mg, 2.0 mmol), tert-butyl[(1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl]methylcarbamate (Method 13; 524 mg, 2.0 mmol), DIPEA (348 μL, 2.0 mmol), HOBT (270 mg, 2.0 mmol) and EDCI (480 mg, 2.5 mmol) were dissolved in DCM (10 mL) and stirred at ambient temperature for 20 hours. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (50 mL), washed with water (3×25 mL), brine (25 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (900 mg, 93%) as a pale brown foam.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. washwashed with water (3×25 mL), brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-61ec1555632c4fa29838f1ed1d29a53d
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122567B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes