Hydrochloric Acid → HCID 66994354, compound

HRID 335143Notes

Reaction equation

HRID 335143 reaction equation
[C:1]1([S:7][C:8]2[C:9]([NH:24][C:25]3[S:29][N:28]=[C:27]([CH:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)[N:26]=3)=[N:10][CH:11]=[C:12]([S:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[CH:22][S:23][C:16]=34)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[ClH:45]>O1CCOCC1>[ClH:45].[ClH:45].[C:1]1([S:7][C:8]2[C:9]([NH:24][C:25]3[S:29][N:28]=[C:27]([CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[N:26]=3)=[N:10][CH:11]=[C:12]([S:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[CH:22][S:23][C:16]=34)[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66994815HCID 66994815, compound

Product 1

HCID 66994354HCID 66994354, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-(5-(3-(phenylthio)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate was dissolved in 1:1CH2Cl2:methanol (4 mL) and 4N HCl in dioxane added (2 mL) and stirred at ambient temperature for 1 hour. The solvent was removed and placed on high vacuum to afford the title compound (100 mg, 89.6% yield) as a yellow solid. 1H NMR (d6-DMSO)S 8.70 (m, 2H), 8.20 (m, 3H), 7.95 (m, 1H), 7.40 (m, 5H), 3.80-3.05 (m, 9H). Mass spectrum (apci) m/z=535.2 (M+H-3HCl).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-bfb1746ad51b4fb690cd8406ca0f6f9c
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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