4-Chlorobenzylamine → HCID 10286976, compound

HRID 982710Notes

Reaction equation

HRID 982710 reaction equation
[OH:1][CH2:2][C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15]CC)=O)=[CH:7][N:6]([CH3:18])[C:5]=2[CH:4]=1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:13]([C:8]2[C:9](=[O:12])[C:10]3[S:11][C:3]([CH2:2][OH:1])=[CH:4][C:5]=3[N:6]([CH3:18])[CH:7]=2)=[O:15])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 22563213HCID 22563213, compound

Product 1

HCID 10286976HCID 10286976, compound

Conditions

Temperature
80 °C

Procedure

Ethyl 2-(hydroxymethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (250 mg, 0.94 mmol) was suspended in 4-chlorobenzylamine (2.0 mL, 16.4 mmol). The mixture was stirred at 80° C. for 16 hours before it was quenched with a mixture of 1.0 M hydrochloric acid (25 mL) and ice (5 g). The mixture was stirred at room temperature for 1 hr. The solid ppt. was collected by vacuum filtration and washed thoroughly with 50 mL of water. Drying in vacuo left a white solid (0.26 g).

Workup

  1. customwas quenched with a mixture of 1.0 M hydrochloric acid (25 mL) and ice (5 g)
  2. stirringThe mixture was stirred at room temperature for 1 hr
  3. filtrationwas collected by vacuum filtration
  4. washwashed thoroughly with 50 mL of water
  5. customDrying in vacuo
  6. waitleft a white solid (0.26 g)

Sources & evidence

ORD record
ord-243f003f19e0476d916817d5721e1f13
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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