Sodium hydride → 1-(2-{3-[(1e)-N-(2-Aminoethoxy)ethanimidoyl]phenyl}propan-2-Yl)-3-(4-Chloro-3-Nitrophenyl)urea

HRID 64223Notes

Reaction equation

HRID 64223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](/[C:21](=[N:23]/[OH:24])/[CH3:22])[CH:16]=2)([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26].[H-].[Na+].Cl.Cl[CH2:32][CH2:33][NH2:34]>CN(C=O)C>[NH2:34][CH2:33][CH2:32][O:24]/[N:23]=[C:21](/[C:17]1[CH:16]=[C:15]([C:12]([NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:25]([O-:27])=[O:26])[CH:4]=2)=[O:10])([CH3:14])[CH3:13])[CH:20]=[CH:19][CH:18]=1)\[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 97937372-Chloroethylamine hydrochlorideHCID 71462574[2-chloro-5-[[1-[3-[(E)-N-hydroxy-C-methyl-carbonimidoyl]phenyl]-1-methyl-ethyl]carbamoylamino]phenyl]azinic acid

Product 1

HCID 714571991-(2-{3-[(1e)-N-(2-Aminoethoxy)ethanimidoyl]phenyl}propan-2-Yl)-3-(4-Chloro-3-Nitrophenyl)ureaYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

(E)-1-(4-Chloro-3-nitrophenyl)-3-(2-(3-(1-(hydroxyimino)ethyl)phenyl)propan-2-yl)urea (7b, 100 mg, 0.25 mmol) in 3 mL dry DMF was added drop wise at 0° C. to sodium hydride dispersion in mineral oil (15.3 mg, 0.50 mmol). The resulting mixture was stirred at 0° C. for 30 min. 2-Chloroethylamine hydrochloride (29.6 mg, 0.25 mmol) in 2 mL DMF was added and the reaction mixture was stirred at room temperature for 2 h and then the volatiles were removed under reduced pressure. The residue was dissolved in a minimal amount of methanol and purified by column chromatography using methanol/chloroform to obtained 9 (49 mg, 46%) 1H NMR (DMSO-d6, 400 MHz) δ 1.61 (s, 6H), 2.19 (s, 3H), 2.79 (t, J=5.6 Hz, 2H), 4.05 (t, J=5.6 Hz, 2H), 6.95 (s, 1H), 7.34 (t, J=7.6 Hz, 1H), 7.42-7.47 (m, 3H), 7.56 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 8.20 (d, J=2 Hz, 1H), 9 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 13.3, 30.1, 41.6, 55.4, 76.6, 113.8, 116.2, 122.7, 122.9, 124.5, 126.3, 128.8, 132.2, 136.5, 141.1, 148.1, 148.8, 154.2, 154.9; ESI-HRMS for C20H24Cl N5O4 (M+H)+ calcd. 434.1595. found. 434.1595.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. customthe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in a minimal amount of methanol
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-647abf1251f94555a5aff3e6ebe7b719
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Reaction notes

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