Cysteamine Hydrochloride → HCID 18416156, compound

HRID 990964Notes

Reaction equation

HRID 990964 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[CH:6]=[C:5]2[C:17]([F:20])([F:19])[F:18].Cl.[NH2:22][CH2:23][CH2:24][SH:25].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[S:25][CH2:24][CH2:23][NH2:22])[N:8]=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[CH:6]=[C:5]2[C:17]([F:20])([F:19])[F:18]

Participants

7

Reactant 4

HCID 9082Cysteamine HydrochlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18416182HCID 18416182, compound

Product 1

HCID 18416156HCID 18416156, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline (0.500 g, 1.36 mmol), 2-aminoethanethiol hydrochloride (0.185 g, 1.63 mmol), NaH (60% in mineral oil, 0.136 g, 3.40 mmol) in 6.8 mL DMF was stirred at 0° C., then allowed to warm to rt. After 4 h, the mixture was poured into a cold saturated NH4Cl:water (60 mL, 1:1). The solution was extracted with EtOAc (2×60 mL), and the combined organic layers washed sequentially with water (30 mL), brine (30 mL), dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 CH2Cl2:MeOH) afforded 0.404 g (73%) of 2-{[6-bromo-2-isopropoxy-4-(trifluoromethyl)-7-quinolinyl]sulfanyl}-1-ethanamine, a yellow-brown solid. Data for 2-{[6-bromo-2-isopropoxy-4-(trifluoromethyl)-7-quinolinyl]sulfanyl}-1-ethanamine: 1H NMR (400 MHz, CDCl3) δ 8.13 (broad s, 1H), 7.63 (s, 1H), 7.10 (s, 1H), 5.54 (hept, 1H, J=6.2), 3.17-3.25 (m, 2H), 3.08-3.15 (m, 2H), 1.41 (d, 6H, J=6.2).

Workup

  1. extractionThe solution was extracted with EtOAc (2×60 mL)
  2. washthe combined organic layers washed sequentially with water (30 mL), brine (30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b89e8d2fb64e4a1e97eae2c1f749fc63
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

Loading…