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Diisopropylethylamine → 3-(4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide

HRID 522915
Notes
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Reaction equation

HRID 522915 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])[CH2:9]2)[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH2:30][C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=1)[C:34]([NH:36][CH3:37])=[O:35]>C(O)(C)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:6]3[N:5]=[CH:4][N:3]=[C:2]([NH:30][C:31]4[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=4)[C:34]([NH:36][CH3:37])=[O:35])[N:7]=3)[CH2:9]2)=[C:14]([F:20])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6765263-Amino-N-methylbenzamideHCID 866852562-Chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazine

Product 1

HCID 533716913-(4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamideYield 53%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazine (0.800 g, 2.54 mmol) [prepared as described for 2-chloro-4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine in Example AAA] in isopropanol (8 mL) was added DIPEA (0.7 mL, 3.81 mmol) and 3-amino-N-methylbenzamide (382 mg, 2.54 mmol). The reaction mixture was stirred at 80° C. for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-(4-(3-(4-chloro-2-fluorophenoxy)azetidin-1-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide (0.537 g, 53%) as a solid. Observed mass (M+1): 428.9.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-62643f8fc06447d3b650c4d56b79c9bc
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09334269B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes