1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,3-Dichloro-5-(N-{(1R,2R)-1-[N-(1,1-dimethylethoxy)carbonylamino]indan-2-yl}carbamoyl)-4H-thieno[3,2-b]pyrrole

HRID 1244727Notes

Reaction equation

HRID 1244727 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][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[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](=[O:3])[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][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[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 11299644tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 114199362,3-Dichloro-5-(N-{(1R,2R)-1-[N-(1,1-dimethylethoxy)carbonylamino]indan-2-yl}carbamoyl)-4H-thieno[3,2-b]pyrroleYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 4; 2.36 g, 10.0 mmol), trans-2-amino-1-{N-[(1,1-dimethylethoxy)]carbonylamino}indan (Method 6; 2.5 g, 10.0 mmol), DIPEA (1.7 ml, 10.0 mmol) and HOBT (1.35 g, 10.0 mmol) was stirred in DCM (75 ml) at room temperature for 2 minutes. EDCI (2.4 g, 12.5 mmol) was added and the mixture stirred at room temperature for 20 hours during which time the product precipitated. The reaction was filtered, washed with DCM (2×25 ml) and dried to give the title compound (3.7 g, 80%) as a pale green powder.

Workup

  1. customprecipitated
  2. filtrationThe reaction was filtered
  3. washwashed with DCM (2×25 ml)
  4. customdried

Sources & evidence

ORD record
ord-5083ec57ba6a4ee5bd0225f6761d534c
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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