Hydrochloric Acid → HCID 86641093, compound

HRID 1809585Notes

Reaction equation

HRID 1809585 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]2[N:9]=[C:10]([NH:13][C:14]3[C:19]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][C:17]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:16][N:15]=3)[S:11][CH:12]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(Cl)Cl.CO.Cl>O1CCOCC1>[CH3:1][CH:2]1[CH:7]([C:8]2[N:9]=[C:10]([NH:13][C:14]3[C:19]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][C:17]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:16][N:15]=3)[S:11][CH:12]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 57742747HCID 57742747, compound

Product 1

HCID 86641093HCID 86641093, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 25 mL flask was charged with tert-butyl 3-methyl-4-(2-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylate (0.296 g, 0.514 mmol), CH2Cl2 (3 mL) and MeOH (3 mL). 4N HCl in dioxane (6 mL) was added and the reaction was stirred for 1 hour and then concentrated. The crude material was dissolved in CH2Cl2 and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated to afford N-(4-(3-methylpiperidin-4-yl)thiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-amine (0.202 g, 82% yield)

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude material was dissolved in CH2Cl2
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d150547aa046b0996784299eb02d58
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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