Hydrochloric Acid → HCID 178489246, compound

HRID 2040109Notes

Reaction equation

HRID 2040109 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]1[S:12][C:13](=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:26]=3[C:33]([F:36])([F:35])[F:34])=[C:20]([O:37][CH3:38])[CH:19]=2)[C:14](=[O:16])[N:15]=1)(C)(C)C.[ClH:40].C(OCC)C>C(OCC)(=O)C.CO>[ClH:40].[NH2:7][CH2:8][CH2:9][NH:10][C:11]1[S:12][C:13](=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:26]=3[C:33]([F:35])([F:34])[F:36])=[C:20]([O:37][CH3:38])[CH:19]=2)[C:14](=[O:16])[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178489244HCID 178489244, compound

Product 1

HCID 178489246HCID 178489246, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

LC/MS (m/z) [M+1]+563.1 (calculated for C26H25F3N4O5S, 562.56). (2-{5-[4-(4-Cyano-2-trifluoromethyl-phenoxy)-3-methoxy-benzylidene]-4-oxo-4,5-dihydro-thiazol-2-ylamino}-ethyl)-carbamic acid tert-butyl ester (0.09 g, 0.14 mmol) was dissolved in a 5/3 mixture of ethyl acetate/methanol (6 mL). To the reaction was then added aqueous 4.0N HCl (4 mL). The reaction mixture was stirred at room temperature for 2 days and the solvent evaporated in vacuo to yield a crude oil. Diethyl ether was added to the residue and the solvent evaporated in vacuo to give a solid which was recrystallized from MeOH and diethyl ether to yield compound as a solid (0.020 g, 30%).

Workup

  1. customthe solvent evaporated in vacuo
  2. customto yield a crude oil
  3. customthe solvent evaporated in vacuo
  4. customto give a solid which
  5. customwas recrystallized from MeOH and diethyl ether

Sources & evidence

ORD record
ord-0b3f92e6eb9a452fb72838420b8c0adc
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

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