Isopropyl chloroformate → HCID 72700243, compound

HRID 710610Notes

Reaction equation

HRID 710610 reaction equation
[O:1]=[C:2]1[C:7]([C:8](O)=[O:9])=[N:6][N:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:12]=2)[C:4]2[N:24]=[CH:25][CH:26]=[CH:27][C:3]1=2.C(Cl)(=O)OC(C)C.[CH:35]1([NH2:38])[CH2:37][CH2:36]1>C(Cl)Cl>[CH:35]1([NH:38][C:8]([C:7]2[C:2](=[O:1])[C:3]3[CH:27]=[CH:26][CH:25]=[N:24][C:4]=3[N:5]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([S:17][C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:12]=3)[N:6]=2)=[O:9])[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 69828CyclopropylamineHCID 118492323HCID 118492323, compound

Product 1

HCID 72700243HCID 72700243, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-oxo-1-(3-(pyridin-3-ylthio)phenyl)-1,4-dihydropyridino[2,3-c]pyridazine-3-carboxylic acid (200 mg, 0.53 mmol) was dissolved in 100 ml of DCM, the following were added dropwise at −15° C. in order: TEA (133.8 mg, 1.325 mmol), isopropyl chlorocarbonate (97 mg, 0.792 mmol), and reacted at −15° C. for 0.5 h, then cyclopropylamine (36 mg, 0.631 mmol) was added dropwise, reacted at room temperature for 3 h. The reaction solution was washed with water, the organic phase was dried, concentrated and crystallized to obtain an object product 13.78 mg.

Workup

  1. additionthe following were added dropwise at −15° C. in order
  2. customreacted at room temperature for 3 h
  3. washThe reaction solution was washed with water
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customcrystallized

Sources & evidence

ORD record
ord-59554c26485742adab2c89142cb289cf
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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