Diisopropylethylamine → N-tert-Butyl-3-((4-(3-fluoro-4-(3-(5-(trifluoromethyl)pyridin-2-yl)ureido)benzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878335Notes

Reaction equation

HRID 1878335 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.C(N(C(C)C)C(C)C)C.[C:21](=O)(OC(Cl)(Cl)Cl)[O:22]C(Cl)(Cl)Cl.[NH2:33][C:34]1[CH:61]=[CH:60][C:37]([C:38]([N:40]2[CH2:45][CH2:44][N:43]([CH2:46][C:47]3[CH:48]=[C:49]([CH:57]=[CH:58][CH:59]=3)[C:50]([NH:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:42][CH2:41]2)=[O:39])=[CH:36][C:35]=1[F:62]>ClCCl>[C:53]([NH:52][C:50](=[O:51])[C:49]1[CH:57]=[CH:58][CH:59]=[C:47]([CH2:46][N:43]2[CH2:44][CH2:45][N:40]([C:38](=[O:39])[C:37]3[CH:60]=[CH:61][C:34]([NH:33][C:21]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]=4)=[O:22])=[C:35]([F:62])[CH:36]=3)[CH2:41][CH2:42]2)[CH:48]=1)([CH3:56])([CH3:55])[CH3:54]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 668785283-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917679N-tert-Butyl-3-((4-(3-fluoro-4-(3-(5-(trifluoromethyl)pyridin-2-yl)ureido)benzoyl)piperazin-1-yl)methyl)benzamideYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Trifluoromethyl)pyridin-2-amine (0.485 mmol, 0.079 g) and N-ethyl-N-isopropylpropan-2-amine (0.727 mmol, 0.120 mL, 0.094 g) were added to a stirred solution of bis(trichloromethyl) carbonate (0.160 mmol, 0.047 g) in dichloromethane (10 mL). The reaction was stirred for 3 hours at room temperature. 3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.242 mmol, 0.1 g) was added and the reaction stirred for 30 minutes. The reaction was heated in the microwave at 120° C. for 10 minutes. The reaction was concentrated under vacuum and purified by acidic reverse phase HPLC to afford the title compound (50 mg).

Workup

  1. stirringthe reaction stirred for 30 minutes
  2. temperatureThe reaction was heated in the microwave at 120° C. for 10 minutes
  3. concentrationThe reaction was concentrated under vacuum
  4. custompurified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-38fdedd871d9409ab6eebf55c88418a9
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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