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Water → 2-(1-{[6-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-5-oxopyrrolidin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 69563
Notes
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Reaction equation

HRID 69563 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]1[CH2:15][N:14]([CH2:16][C:17]2[N:24]3[C:20]([S:21][C:22]([CH2:25][O:26][CH3:27])=[N:23]3)=[N:19][C:18]=2[Cl:28])[C:13](=[O:29])[CH2:12]1)C1C=CC=CC=1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31].C(N(CC)CC)C.O>FC(F)(F)C(O)=O.CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:37][C:36]1[CH:38]=[CH:39][C:33]([S:30]([O:8][CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:29])[N:14]([CH2:16][C:17]3[N:24]4[C:20]([S:21][C:22]([CH2:25][O:26][CH3:27])=[N:23]4)=[N:19][C:18]=3[Cl:28])[CH2:15]2)(=[O:32])=[O:31])=[CH:34][CH:35]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67116479HCID 67116479, compound

Product 1

HCID 866714522-(1-{[6-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-5-oxopyrrolidin-3-yl)ethyl 4-methylbenzenesulfonateYield 89%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

4-[2-(benzyloxy)ethyl]-1-{[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one a37 (300 mg, 0.69 mmol, 1 eq) is heated at 60° C. for 3 hours in trifluoroacetic acid (3 ml). The crude 1-{[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(2-hydroxyethyl)pyrrolidin-2-one a38 is obtained after cooling and evaporation of the volatiles under reduced pressure. Dichloromethane (10 ml) is added to the residue, the mixture is cooled to 0° C., then tosyl chloride (158 mg, 0.828 mmol, 1.2 eq), triethyl amine (0.48 ml, 3.45 mmol, 5 eq) and 4-dimethylamino-pyridine (8 mg, 10 mol %,) are added at 0° C. The reaction is kept for 1 h at 0° C., then warmed up to room temperature and stirring is pursued for 2 days. After hydrolysis (H2O, 10 ml) and extraction with CH2Cl2 (4×10 ml), the cumulated organic layers are dried over MgSO4, filtered and evaporated under reduced pressure. The residue is purified by flash chromatography over silicagel (eluent: CH2Cl2/MeOH 97:3) to afford 308 mg of 2-(1-{[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-5-oxopyrrolidin-3-yl)ethyl 4-methylbenzenesulfonate a39.

Workup

  1. customThe crude 1-{[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(2-hydroxyethyl)pyrrolidin-2-one a38 is obtained
  2. temperatureafter cooling
  3. customevaporation of the volatiles under reduced pressure
  4. additionDichloromethane (10 ml) is added to the residue
  5. temperaturewarmed up to room temperature
  6. waitis pursued for 2 days
  7. dry with materialthe cumulated organic layers are dried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue is purified by flash chromatography over silicagel (eluent: CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-09925e9978a241578ee4a82da8e9086c
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822508B2

Reaction notes

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