1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-[(1R,2R)-1-({[(2S)-5-oxotetrahydrofuran-2-yl]carbonyl}amino)-2,3-dihydro-1H-inden-2-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1244717Notes

Reaction equation

HRID 1244717 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[O:20]=[C:21]1[O:25][C@H:24]([C:26]([OH:28])=O)[CH2:23][CH2:22]1.CCN=C=NCCCN(C)C.[NH2:40][C@@H:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43][C@H:42]1[NH:50][C:51]([C:53]1[NH:57][C:56]2[S:58][C:59]([Cl:61])=[CH:60][C:55]=2[CH:54]=1)=[O:52]>C(Cl)Cl>[Cl:61][C:59]1[S:58][C:56]2[NH:57][C:53]([C:51]([NH:50][C@@H:42]3[CH2:43][C:44]4[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=4)[C@H:41]3[NH:40][C:26]([C@@H:24]3[CH2:23][CH2:22][C:21](=[O:20])[O:25]3)=[O:28])=[O:52])=[CH:54][C:55]=2[CH:60]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 636468(2S)-5-oxooxolane-2-carboxylic acidHCID 58717470N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 102882562-Chloro-N-[(1R,2R)-1-({[(2S)-5-oxotetrahydrofuran-2-yl]carbonyl}amino)-2,3-dihydro-1H-inden-2-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (180 μL, 1.05 mmol), HOBT (68 mg, 0.5 mmol), (2S)-5-oxotetrahydrofuran-2-carboxylic acid (CAS Reg. No: [21461–84–7], 0.5 mmol, 65 mg) and EDAC (120 mg, 0.63 mmol) were added to a suspension of N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 21, 223 mg, 0.5 mmol) in anhydrous DCM (7 mL). The reaction was stirred at ambient temperature for approximately 16 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (5 mL), washed with water (2×5 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue triturated (EtOAc:hexane, 1:10), collected by filtration, washed with hexane (2×5 mL) and dried to give the title compound (112 mg, 56%) as a brown solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (5 mL)
  3. washwashed with water (2×5 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue triturated (EtOAc:hexane, 1:10)
  7. filtrationcollected by filtration
  8. washwashed with hexane (2×5 mL)
  9. customdried

Sources & evidence

ORD record
ord-e350f731bcbc4e7b9aa6480e5df2a170
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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