1-(4-Chlorophenyl)cyclopropanamine → Tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

HRID 876641Notes

Reaction equation

HRID 876641 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH:14][C:15]2[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:17][CH:16]=2)[N:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2([NH2:38])[CH2:37][CH2:36]2)=[CH:31][CH:30]=1>C1COCC1>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2([NH:38][C:2]3[N:7]=[C:6]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[N:5]=[C:4]([NH:14][C:15]4[CH:16]=[CH:17][C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[CH:26][CH:27]=4)[N:3]=3)[CH2:36][CH2:37]2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 113442131-(4-Chlorophenyl)cyclopropanamineHCID 86652471Tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Product 1

HCID 66766356Tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoateYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (3.6 g) and 1-(4-chlorophenyl)cyclopropanamine (1.49 g) in THF (50 mL) was stirred for 5 hours at 80° C. The precipitate was filtrated through a plug washing with THF to give acrude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.8 g of tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate as a solid.

Workup

  1. filtrationThe precipitate was filtrated through a plug
  2. washwashing with THF
  3. customto give acrude product that
  4. customwas purified by Biotage
  5. washeluting with 4/1-hexane/ethyl acetate

Sources & evidence

ORD record
ord-a18135de19004a318df3380f7fe76d83
Source dataset
uspto-grants-2015_03
Patent number
US08987264B2

Reaction notes

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