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Acetic Anhydride → HCID 11711523, compound

HRID 1781992
Notes
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Reaction equation

HRID 1781992 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[S:11]([N:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH2:24][NH2:25])=[CH:15]1)(=[O:13])=[O:12])[CH:8]=[CH:7][S:6]2.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34].C([O-])(O)=O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[S:11]([N:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH2:24][NH:25][C:33](=[O:35])[CH3:34])=[CH:15]1)(=[O:12])=[O:13])[CH:8]=[CH:7][S:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 222197352-[1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl]ethylamine Hydrochloride

Product 1

HCID 11711523HCID 11711523, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethylamine hydrochloride, 417 mg, 1.00 mmol) in dichloromethane and triethylamine (0.40 mL, 3.0 mmol) is treated with catalytic 4-dimethylaminopyridine (DMAP) (˜5 mg) at room temperature under nitrogen. The heterogeneous mixture is treated with acetic anhydride (0.30 mL, 3.2 mmol) and the reaction becomes homogeneous. After 16 h, the reaction is treated with saturated aqueous NaHCO3 (8 mL) for 0.3 h and then extracted with dichloromethane. The extracts are combined, dried over MgSO4 and concentrated in vacuo to a foam. The foam is treated with 20:80 ethyl acetate:hexane and concentrated in vacuo to a solid. This is triturated with ether and filtered. The filtercake is dried to afford the title product as a white solid, 389 mg (92% yield), mp 150-152° C., characterized by CHN elemental analysis and 1H NMR.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo to a foam
  4. additionThe foam is treated with 20:80 ethyl acetate
  5. concentrationhexane and concentrated in vacuo to a solid
  6. customThis is triturated with ether
  7. filtrationfiltered
  8. customThe filtercake is dried

Sources & evidence

ORD record
ord-7607adb8172842e19e814c4670b1e131
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07498327B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes