1-Chloro-N,N-2-trimethylpropenylamine → HCID 52919088, compound

HRID 1846094Notes

Reaction equation

HRID 1846094 reaction equation
ClC(N(C)C)=C(C)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[C:19]2[CH:24]=[C:23]([CH2:25][NH:26][C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:28])[CH:22]=[CH:21][C:20]=2[Cl:33])=[CH:13][C:12]=1[C:35]([OH:37])=O.[NH2:38][C:39]1[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[CH:41][N:40]=1>C1COCC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[C:19]2[CH:24]=[C:23]([CH2:25][NH:26][C:27]([C:29]([CH3:31])([CH3:32])[CH3:30])=[O:28])[CH:22]=[CH:21][C:20]=2[Cl:33])=[CH:13][C:12]=1[C:35]([NH:38][C:39]1[CH:44]=[C:43]([C:45]([F:47])([F:46])[F:48])[CH:42]=[CH:41][N:40]=1)=[O:37]

Participants

5

Reactant 3

HCID 6407921-Chloro-N,N-2-trimethylpropenylamine2×HCID 27783152-Amino-4-(trifluoromethyl)pyridineHCID 58483461HCID 58483461, compound

Product 1

HCID 52919088HCID 52919088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Chloro-N,N,2-trimethylpropenylamine (23 was added to a mixture of N-[4-methoxy-3-hydroxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide (60.0 mg, 0.143 mmol, prepared from ethyl 5-amino-2-methoxy benzoate in analogy to step 5c and 5d) in 2.0 mL THF and it was stirred for 2 h. additional 80 μL of 1-chloro-N,N,2-trimethylpropenylamine were added and it was stirred for another 2 h. Then TEA (0.100 mL) and 2-amino-4-trifluormethyl-pyridine (23.2 mg, 0.143 mmol) were added and it was stirred overnight. The reaction mixture was concentrated and purified via prep. HPLC (method A) to furnish the title compound.

Workup

  1. additionwere added
  2. stirringit was stirred overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompurified via prep

Sources & evidence

ORD record
ord-bd45c028130b4ca7a0d88afde9aa86c1
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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