Water → 5-Chloro-N-{2-[(2-hydroxyethyl)phenylamino]-2-oxoethyl}-1H-indole-2-carboxamide

HRID 1242119Notes

Reaction equation

HRID 1242119 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH2:14][C:15]([OH:17])=O)=[O:12])=[CH:5]2.[C:18]1([NH:24][CH2:25][CH2:26][OH:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH2:14][C:15]([N:24]([CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])=[O:12])=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 31235N-(2-Hydroxyethyl)anilineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine

Product 1

HCID 102372415-Chloro-N-{2-[(2-hydroxyethyl)phenylamino]-2-oxoethyl}-1H-indole-2-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine (Cas Reg No 186429-62-9; Hulin, Bernard, et al, PCT International Patent Application (1996) WO 9639384; 374 mg, 1.5 mmol) and 2-(phenylamino)ethanol (228 mg, 1.6 mmol) in THF (20 ml) was stirred at ambient temperature for 30 minutes. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)4-methylmorpholinium chloride (DMTMM) (480 mg, 1.6 mmol) was added and the reaction mixture stirred at ambient temperature overnight, poured into water (15 ml) and extracted with ethyl acetate (3×15 ml). The organic extracts were combined and washed with 1N citric acid solution (15 ml), sodium bicarbonate solution (15 ml), dried over magnesium sulphate, filtered and concentrated to give the title product (471 mg, 86%).

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. washwashed with 1N citric acid solution (15 ml), sodium bicarbonate solution (15 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-694abaeb6bac4c1085035d2fbf875d1b
Source dataset
uspto-grants-2006_10
Patent number
US07115648B2

Reaction notes

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