1-Chloro-N,N-2-trimethylpropenylamine → HCID 86665216, compound

HRID 578059Notes

Reaction equation

HRID 578059 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH:3]=1.ClC(N(C)C)=C(C)C.[NH2:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([N:39]([CH3:41])[CH3:40])[N:30]=1>C1COCC1>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH:28][C:29]2[CH:34]=[C:33]([C:35]([F:36])([F:38])[F:37])[CH:32]=[C:31]([N:39]([CH3:41])[CH3:40])[N:30]=2)=[O:8])=[C:4]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH:3]=1

Participants

5

Reactant 3

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 67230258HCID 67230258, compoundHCID 67231343HCID 67231343, compound

Product 1

HCID 86665216HCID 86665216, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product obtained at (656b) (15.5 g, 2.97 mmol) in 3 mL THF was combined with (1-Chlor-2-methyl-prop-1-en-1-yl)-dimethylamine (0.14 mL, 1.1 mmol) and stirred at ambient temperature for 1 h. Then a mixture of 2-amino-6-dimethylamino-4-trifluoromethyl-pyridine (0.19 g, 0.94 mmol) with TEA (0.50 mL, 3.6 mmol) in 5 mL THF was added and the mixture stirred at ambient temperature for 16 h. The mixture was filtered, evaporated, the residue was mixed with diethylether, filtered off, washed with diethylether and dried.

Workup

  1. additionwas added
  2. stirringthe mixture stirred at ambient temperature for 16 h
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. additionthe residue was mixed with diethylether
  6. filtrationfiltered off
  7. washwashed with diethylether
  8. customdried

Sources & evidence

ORD record
ord-92fd2079073e4807a62c18d70695b815
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

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