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Triethylamine → HCID 10288257, compound

HRID 1244722
Notes
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Reaction equation

HRID 1244722 reaction equation
FC(F)(F)C(O)=O.[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].CCN(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40].C([O-])(O)=O.[Na+]>C1COCC1>[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][S:39]([CH3:38])(=[O:41])=[O:40])=[O:20])[NH:25][C:24]=2[C:26]=1[Cl:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69545963HCID 69545963, compound

Product 1

HCID 10288257HCID 10288257, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

N-[(1R,2R)-1-Amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide trifluoroacetate salt (Method 8, 223 mg, 0.5 mmol) was dissolved in THF (4 mL) and the solution cooled to 0° C. Et3N (223 μL, 1.6 mmol) then methanesulfonyl chloride (43 μL, 0.55 mmol) were added and the reaction was stirred 0° C. for 5 mins. Saturated aqueous NaHCO3 (5 mL) was added, the phases separated and the aqueous phase extracted with EtOAc (3×10 mL). The combined organic fractions were washed with H2O (20 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was subjected to purification by reverse phase preparative HPLC to afford the title compound (30 mg, 15%) as a white solid.

Workup

  1. customthe phases separated
  2. extractionthe aqueous phase extracted with EtOAc (3×10 mL)
  3. washThe combined organic fractions were washed with H2O (20 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue was subjected to purification by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-43609dc4ae334b44921216979f1f73e0
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122567B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes