Diisopropylethylamine → HCID 67147358, compound

HRID 2426077Notes

Reaction equation

HRID 2426077 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:22][CH3:23])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=2[S:18]([CH3:21])(=[O:20])=[O:19])[CH3:9])[CH:7]=1.[NH:26]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:22][CH3:23])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:26]3[CH2:30][CH2:29][C@@H:28]([NH2:31])[CH2:27]3)[CH:14]=[CH:13][C:12]=2[S:18]([CH3:21])(=[O:20])=[O:19])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1644013-AminopyrrolidineHCID 44240863N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

Product 1

HCID 67147358HCID 67147358, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine (100.0 mg, 0.26 mmol), pyrrolidin-3-amine (86.1 mg, 0.51 mmol), N,N-diisopropylethylamine (133.0 mg, 1.03 mmol) were stirred at 100° C. in dry acetonitrile (3 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 10% methanol in dichloromethane to afford the title compound (50.0 mg, 42.8% yield). 1H NMR (400 MHz, CDCl3): δ 7.52 (d, 1H), 6.88 (d, 1H), 6.76 (d, 1H), 6.51 (d, 1H), 6.89 (dd, 1H), 4.84 (m, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.64 (m, 1H), 3.46-2.84 (m, 4H), 3.04 (s, 3H), 2.12 (m, 1H), 2.01 (s, 3H), 1.75, (m, 1H), 1.53 (d, 3H); MS (ESI) m/z: 454.1 (M+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

Sources & evidence

ORD record
ord-2a668cb05c774adab1836436a928b7f8
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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