Hydrochloric Acid → HCID 86639690, compound

HRID 1426151Notes

Reaction equation

HRID 1426151 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:22][CH:23]=[O:24])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-:26].Cl>CCO>[ClH:26].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:22][CH2:23][OH:24])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 59225671HCID 59225671, compound

Product 1

HCID 86639690HCID 86639690, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 20 mL vial was charged with 2-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acetaldehyde (50 mg, 0.15 mmol), NaBH (11 mg, 0.29 mmol), and EtOH (2 mL). The reaction was stirred at room temperature for 10 minutes and aqueous NH4Cl was added. The mixture was extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (1:1 EtOAc:Hexanes) to afford the title compound (37 mg, 66% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 11.03 (bs, 1H), 7.85 (d, 1H), 7.59 (t, 3H), 7.45-7.33 (m, 3H), 6.83 (s, 1H), 5.31 (s, 2H), 3.61 (t, 2H), 2.72 (t, 2H), 2.32 (s, 3H). Mass spectrum (apci) m/z=342.1 (M+H-HCl).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel (1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-4e6432e13d374a5198d7a05f2bb428db
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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