Isopropyl chloroformate → HCID 44219498, compound

HRID 1928832Notes

Reaction equation

HRID 1928832 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]>C1(C)C=CC=CC=1.O>[CH:33]([O:32][C:30](=[O:31])[NH:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:10][C@H:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]1)[CH:20]=[CH:19]2)([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44219498HCID 44219498, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

(R)—N2-indan-1-yl-quinoline-2,6-diamine (0.07 g, 0.25 mmol), triethylamine (0.052 mL, 0.38 mmol) and isopropyl chloroformate (1M solution in toluene) (0.281 mL, 0.28 mmol) were dissolved in toluene (3 mL) and stirred at 60° C. for 10 h. The reaction mixture was diluted with water and extracted with ethyl acetate (10 mL). The combined organic phases was dried over sodium sulfate, filtered and the filtrate evaporated. The residue was subjected to column chromatography (silica gel, heptane/ethyl acetate, 9:1, 4:1, 3:1) to yield the title compound (0.026 g, 41%) as a white foam; MS: m/e=361.7 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (10 mL)
  2. dry with materialThe combined organic phases was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-2aef8509f76348c2829e660053b17371
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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