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Hydrochloric Acid → N-(4-methylthiazol-2-yl)-3-(phenylthio)-5-((tetrahydropyran-4-ylidene)methyl)pyridin-2-amine hydrochloride

HRID 335131
Notes
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Reaction equation

HRID 335131 reaction equation
[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH:15]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)O)=[CH:11][C:10]=2[S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:6][CH:7]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.Cl>C1(C)C=CC=CC=1>[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([NH:8][C:9]2[C:10]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:11][C:12]([CH:15]=[C:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][N:14]=2)[S:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 86631490(6-(4-methylthiazol-2-ylamino)-5-(phenylthio)Pyridin-3-yl)(tetrahydro-2H-pyran-4-yl)methanol hydrochloride

Product 1

HCID 86631492N-(4-methylthiazol-2-yl)-3-(phenylthio)-5-((tetrahydropyran-4-ylidene)methyl)pyridin-2-amine hydrochlorideYield 35%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

A 10 mL round-bottomed flask was charged with (6-(4-methylthiazol-2-ylamino)-5-(phenylthio)pyridin-3-yl)(tetrahydro-2H-pyran-4-yl)methanol hydrochloride (125 mg, 0.278 mmol), 4-methylbenzenesulfonic acid hydrate (5.28 mg, 0.0278 mmol), Toluene (5 mL) and heated to reflux in dean stark trap for 24 7 hours. The reaction was cooled to ambient temperature and partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (25% EtOAc in hexanes) to afford the title compound (42 mg, 35.0% yield) as after HCl salt formation. 1H NMR (CDCl3) δ 12.24 (bs, 1H), 8.18 (m, 1H), 7.71 (m, 1H), 7.54 (m, 2H), 7.30 (m, 3H), 6.40 (s, 1H), 6.20 (s, 1H), 3.78 (t, 2H), 3.65 (t, 2H), 2.45 (s, 3H), 2.42 (m, 4H). Mass spectrum (apci) m/z=396.2 (M+H—HCl).

Workup

  1. temperatureheated
  2. temperatureto reflux in dean stark trap for 24 7 hours
  3. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a078e5939b5f4e918f1b9f700a046a25
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883828B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes