Formic Acid → HCID 10237564, compound

HRID 1244709Notes

Reaction equation

HRID 1244709 reaction equation
FC(F)(F)[C:3](O)=[O:4].[NH2:8][C@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@@H:10]1[NH:18][C:19]([C:21]1[NH:25][C:24]2[C:26]([Cl:30])=[C:27]([Cl:29])[S:28][C:23]=2[CH:22]=1)=[O:20].C(O)=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:29][C:27]1[S:28][C:23]2[CH:22]=[C:21]([C:19]([NH:18][C@H:10]3[CH2:11][C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C@@H:9]3[NH:8][CH:3]=[O:4])=[O:20])[NH:25][C:24]=2[C:26]=1[Cl:30]

Participants

7

Reactant 5

HCID 284Formic Acid2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69546008HCID 69546008, compound

Product 1

HCID 10237564HCID 10237564, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1S,2S)-1-Amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide trifluoroacetic acid salt (Method 9, 240 mg, 05 mmol), formic acid (50 μL, 1.4 mmol), DIPEA (174 μL, 1.0 mmol) and HOBT (67 mg, 0.5 mmol) were dissolved in DCM (5 ml), stirred for 5 mins, EDCI (120 mg, 0.625 mmol) added and the reaction stirred for 1 hr. Formic acid (50 μL, 1.4 mmol) and EDCI (240 mg, 1.25 mmol) were added, the reaction stirred for 2 hours and the volatiles removed by evaporation under reduced pressure. The residue was dissolved in EtOAc (20 mL), washed with water (2×10 mL), brine (10 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure. The residue was purified by column chromatography (2:1 EtOAc:Hexane) to afford the title compound (180 mg, 97%) as a white foam.

Workup

  1. stirringthe reaction stirred for 1 hr
  2. stirringthe reaction stirred for 2 hours
  3. customthe volatiles removed by evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (20 mL)
  5. washwashed with water (2×10 mL), brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customthe volatiles removed by evaporation under reduced pressure
  8. customThe residue was purified by column chromatography (2:1 EtOAc:Hexane)

Sources & evidence

ORD record
ord-1b8fe15f14cc4b749115904eec77588f
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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