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Formic Acid → HCID 9821978, compound

HRID 1244704
Notes
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Reaction equation

HRID 1244704 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 284Formic Acid2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69545963HCID 69545963, compound

Product 1

HCID 9821978HCID 9821978, compound
Yield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1R,2R)-1-Amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide trifluoroacetic acid salt (Method 8, 240 mg, 0.5 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 (175 mg, 89%) 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-e4957ff7e51f4ea4b78f23fcd1392658
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122567B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes