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

HRID 911800Notes

Reaction equation

HRID 911800 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-27d1e3b005dd4ad0b928991898355a5e
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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