1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl((1R,2R)-2-{[(2-Chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 1244734Notes

Reaction equation

HRID 1244734 reaction equation
[Cl:1][C:2]1[S:9]C2CC(C(O)=O)=NC=2[CH:3]=1.[NH2:13][C@@H:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:15]1[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].CC[N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])[CH3:35].C1C=CC2N([OH:49])N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:27]([O:26][C:24](=[O:25])[NH:23][C@@H:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][C@H:14]1[NH:13][C:36]([C:34]1[NH:33][C:37]2[S:9][C:2]([Cl:1])=[CH:3][C:39]=2[CH:35]=1)=[O:49])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11299644tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamateHCID 219204592-Chloro-5-carboxy-6h-thieno[3,2-b]pyrrole

Product 1

HCID 58717460tert-Butyl((1R,2R)-2-{[(2-Chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-carboxy-6H-thieno[3,2-b]pyrrole (Method 4a, 5.0 g, 25.0 mmol), trans-2-amino-1-[(1,1-dimethylethoxy)carbonylamino]indan (Method 6, 6.25 g, 25.0 mmol), DIPEA (4.35 mL, 25.0 mmol) and HOBT (3.4 g, 25.0 mmol) were dissolved in DCM (200 mL) and stirred for 5 mins. EDCI (6.0 g, 31.0 mmol) was added, the reaction stirred for 24 hours and evaporated under reduced pressure. EtOAc (150 mL) was added and the mixture filtered, washed with water (2×200 mL), brine (200 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure to give the title compound (10.6 g, 98%) as a brown solid.

Workup

  1. stirringthe reaction stirred for 24 hours
  2. customevaporated under reduced pressure
  3. additionEtOAc (150 mL) was added
  4. filtrationthe mixture filtered
  5. washwashed with water (2×200 mL), brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. customthe volatiles removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-34565f2e30f949f288a85958ae49d105
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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