Hydrochloric Acid → HCID 86731673, compound

HRID 1504783Notes

Reaction equation

HRID 1504783 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)[N:10]=1)C1C=CC=CC=1.C(NC1C=C(C)C=C(N2C=CN=N2)N=1)C1C=CC=CC=1.Cl.[H][H].[OH-].[Na+]>CO.[Pd]>[CH3:15][C:13]1[CH:12]=[C:11]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)[N:10]=[C:9]([NH2:8])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86731674HCID 86731674, compoundHCID 86731675HCID 86731675, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86731673HCID 86731673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 1:1 regioisomeric mixture of N-benzyl-4-methyl-6-(2H-1,2,3-triazol-2-yl)pyridin-2-amine (316 mg, 1.19 mmol) and N-benzyl-4-methyl-6-(1H-1,2,3-triazol-1-yl)pyridin-2-amine (316 mg, 1.19 mmol) from the previous step was dissolved in methanol (10 mL). Hydrochloric acid (37% in water, 1.96 mL, 23.8 mmol) and palladium on carbon (127 mg, 0.119 mmol, 10 wt %) were added. The flask was fitted with a hydrogen balloon and evacuated and backfilled with hydrogen (3×). The reaction mixture was stirred under an atmosphere of hydrogen for 14 hours. The reaction mixture was filtered, diluted with sodium hydroxide (1.0 M in water, 30 mL, 30 mmol), and extracted with ethyl acetate (3×). The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (25-50% ethyl acetate/hexanes, linear gradient) afforded 4-methyl-6-(2H-1,2,3-triazol-2-yl)pyridin-2-amine. MS ESI calc'd. for C8H10N5 [M+H]+ 176. found 176. 1H NMR (500 MHz, CD3OD) δ 7.93 (s, 2H), 7.11 (s, 1H), 6.40 (s, 1H), 2.30 (s, 3H).

Workup

  1. customevacuated
  2. filtrationThe reaction mixture was filtered
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (25-50% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-b1584831905048aeb9b0fc2e3052a2b8
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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