Ammonium Chloride → (6-(4-Methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)methanol

HRID 335113Notes

Reaction equation

HRID 335113 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:15]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][N:9]=2)[S:5][CH:6]=1.[BH4-].[Na+].[NH4+].[Cl-]>CCO>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:14][C:15]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866314726-(4-Methylthiazol-2-ylamino)-5-phenoxynicotinaldehyde

Product 1

HCID 57742952(6-(4-Methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)methanolYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of mL 6-(4-methylthiazol-2-ylamino)-5-phenoxynicotinaldehyde (Example 44, Step A; 150 mg, 0.48 mmol) and EtOH (5 mL) was added sodium borohydride (27.3 mg, 0.72 mmol) and stirred at ambient temperature for 30 minutes. Poured into saturated aqueous NH4Cl and extracted with CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (1:1 EtOAc:hexanes) to afford the title compound (132 mg, 87.4% yield) as a white solid. 1H NMR (CDCl3) δ 8.66 (bs, 1H), 8.06 (d, 1H), 7.38 (m, 2H), 7.19 (m, 1H), 7.12 (d, 1H), 7.03 (m, 2H), 6.42 (q, 1H), 4.58 (s, 2H), 2.33 (d, 3H), 1.77 (bs, 1H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-0584204b7b8644f097e7dc81e09ffe55
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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