Isopropylamine → HCID 22181351, compound

HRID 1796511Notes

Reaction equation

HRID 1796511 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([NH:20][CH3:21])[CH:17]=[CH:16][C:15]=2[N+:22]([O-:24])=[O:23])=[O:12])=[CH:6][CH:5]=1)[CH3:2].ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[CH:37]([NH2:40])([CH3:39])[CH3:38]>ClCCCl.CN(C1C=CN=CC=1)C>[CH3:21][N:20]([C:29]([NH:40][CH:37]([CH3:39])[CH3:38])=[O:35])[C:18]1[CH:17]=[CH:16][C:15]([N+:22]([O-:24])=[O:23])=[C:14]([NH:13][C:11](=[O:12])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=2)[CH:19]=1

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 94429TriphosgeneHCID 22181284HCID 22181284, compound

Product 1

HCID 22181351HCID 22181351, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4-ethoxy-N-[5-(methylamino)-2-nitrophenyl]-benzeneacetamide (2.20 g, 6.69 mmol) in 1,2-dichloroethane (100 mL) was stirred at room temperature under nitrogen as triphosgene (1.99 g, 6.69 mmol) and TEA (0.93 mL, 6.69 mmol) were added. After 30 minutes, DMAP (817 mg, 6.69 mmol), and isopropylamine (3.42 mL, 40.0 mmol) were added, and the contents were stirred for 16 hours at 45° C. The mixture was quenched with saturated aqueous NaHCO3 (40 m L) and the layers were separated. The aqueous phase was extracted with dichloromethane (2×50 mL) and the organic layers were combined and washed with brine (50 mL), and dried with Na2SO4. The solids were filtered off and the filtrate concentrated in vacuo to a residue which was purified by column chromatography (75% EtOAc, 25% heptane on silica gel) to give the title compound (2.44 g, 88%), 1HNMR (400 MHz, CDCl3): δ 1.14 (d, J=6.4, 6H), 1.38 (t, J=7.1 Hz, 3H), 3.29 (s, 3H), 3.71 (s, 2H), 4.01 (q, J=7:1 Hz, 2H), 4.70 (s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.00 (dd, J=2.5, 9.2 Hz, 1H), 7.22 (d, J=8.8 Hz, 2H), 8.13 (d, J=9.2 Hz, 1H), 8.61 (d, J=2.5 Hz, 1H). MS (ESI) (M+H)+=415.

Workup

  1. additionwere added
  2. customThe mixture was quenched with saturated aqueous NaHCO3 (40 m L)
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with dichloromethane (2×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried with Na2SO4
  7. filtrationThe solids were filtered off
  8. concentrationthe filtrate concentrated in vacuo to a residue which
  9. customwas purified by column chromatography (75% EtOAc, 25% heptane on silica gel)

Sources & evidence

ORD record
ord-483a9dafd00641e594b05b70761871bd
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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