Water → HCID 14013855, compound

HRID 1649699Notes

Reaction equation

HRID 1649699 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](Br)[C:4]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33].O>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]([NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])[C:4]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 14013849HCID 14013849, compound

Product 1

HCID 14013855HCID 14013855, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.0 g (0.015 mol) of product from Example 106, 1.48 g (0.0147 mol) of triethylamine and 2.15 g (0.0244 mol) of t-butylamine in 30 ml of DMF was stirred at 50° C. for 12 hours. The reaction mixture was poured into H2O, and extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4). The dry ether phase was concentrated in vacuo to 2.8 g of a brown oil. The crude product was kugelrohr distilled at 67 Pa and collected at a pot temperature of 154°-155° C. affording 2.5 g (42%) of product as a beige solid; mp 30°-31° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationThe dry ether phase was concentrated in vacuo to 2.8 g of a brown oil
  5. distillationThe crude product was kugelrohr distilled at 67 Pa
  6. customcollected at a pot temperature of 154°-155° C.

Sources & evidence

ORD record
ord-7c3b5cf6e2134ddc90b19602186cfffd
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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