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Ammonium Chloride → 3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochloride

HRID 1426106
Notes
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Reaction equation

HRID 1426106 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][O:13][C:14]1[C:15]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-:49]>C1COCC1>[ClH:49].[CH3:26][C:24]1[N:25]=[C:21]([NH:20][C:15]2[C:14]([O:13][CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)[S:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 727058253-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

Product 1

HCID 866396593-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A 125 mL round-bottomed flask was charged with 3-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (5.4 g, 13 mmol) and THF (50 mL). TBAF (1M in THF, 15 mL, 15 mmol) was added and stirred at room temperature overnight. The reaction was poured into saturated aqueous NH4Cl and extracted with CH2Cl2 (2×100 mL). The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified over silica gel (30 to 80% EtOAc in hexanes) to afford 3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochloride (3.5 g, 79%) after HCl salt formation. 1H NMR (d6-DMSO) δ 9.83 (bs, 1H), 9.50 (bs, 1 h), 7.89 (dd, 1H), 7.38 (d, 1H), 7.22 (t, 1H), 6.98 (m, 2H), 6.91 (dd, 1H), 6.75 (dd, 1H), 6.62 (s, 1H), 5.22 (s, 2H), 2.29 (s, 3H). Mass spectrum (apci) m/z=314.1 (M+H-HCl).

Workup

  1. extractionextracted with CH2Cl2 (2×100 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified over silica gel (30 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2e20642a36ed4274967f1da790f16cb2
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933077B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes