Trifluoroacetic acid → N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1244733Notes

Reaction equation

HRID 1244733 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[NH:17][C:18]([C:20]1[NH:24][C:23]2[S:25][C:26]([Cl:28])=[CH:27][C:22]=2[CH:21]=1)=[O:19])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[NH:17][C:18]([C:20]1[NH:24][C:23]2[S:25][C:26]([Cl:28])=[CH:27][C:22]=2[CH:21]=1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58717460tert-Butyl((1R,2R)-2-{[(2-Chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 58717470N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 134.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (Method 22, 10.6 g, 24.5 mmol) was suspended in DCM (200 mL), TFA (20 mL) added and the reaction stirred at ambient temperature for 20 hours. The volatiles were removed by evaporation under reduced pressure and the residue triturated with DCM (50 mL) then filtered and dried to give the title compound (10.9 g, 100%) as the trifluoroacetic acid salt.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. customthe residue triturated with DCM (50 mL)
  3. filtrationthen filtered
  4. customdried

Sources & evidence

ORD record
ord-eb50ff18a4cc4f04a8d66617580ae58f
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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