Hydrochloric Acid → HCID 14013854, compound

HRID 1763156Notes

Reaction equation

HRID 1763156 reaction equation
[F:1][CH:2]([F:24])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5](Cl)[C:4]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C.[CH3:32][NH:33][CH:34]1[CH2:36][CH2:35]1.Cl>CN(C=O)C>[F:1][CH:2]([F:24])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([N:33]([CH:34]2[CH2:36][CH2:35]2)[CH3:32])[C:4]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11029756N-MethylcyclopropanamineHCID 14013848HCID 14013848, compound

Product 1

HCID 14013854HCID 14013854, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6.0 g (0.017 mol) of product from Example 105, 1.71 g (0.017 mol) of triethylamine in 30 ml of DMF was added 1.76 g (0.025 mol) of N-methylcyclopropylamine at such a rate that the temperature remained below 30° C. After 4 hours the reaction mixture was poured into 3.7% HCl and extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4). The dry ether phase was concentrated in vacuo to 5.8 g of a green oil. The crude product was purified by HPLC in 5% ethyl acetate/cyclohexane, followed by kugelrohr distillation at 67 Pa, oven temperature 150° C., affording 1.02 g (15.5%) of product as a green oil, nD25 1.4758.

Workup

  1. customremained below 30° C
  2. extractionextracted with diethyl ether
  3. washThe ether phase was washed with H2O
  4. dry with materialdried (MgSO4)
  5. concentrationThe dry ether phase was concentrated in vacuo to 5.8 g of a green oil
  6. customThe crude product was purified by HPLC in 5% ethyl acetate/cyclohexane
  7. distillationfollowed by kugelrohr distillation at 67 Pa, oven temperature 150° C.

Sources & evidence

ORD record
ord-c733994aebe14b40a098a98c0339c460
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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