3-Chloro-4-fluoroaniline → HCID 57708238, compound

HRID 404822Notes

Reaction equation

HRID 404822 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])[NH2:26]>CCOC(C)=O>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:2]2[CH:3]=[C:4]([NH:8][CH:9]3[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]3)[N:5]=[CH:6][N:7]=2)[CH:27]=[CH:28][C:29]=1[F:30]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 22309474tert-Butyl 3-((6-chloropyrimidin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 57708238HCID 57708238, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl 3-(6-chloropyrimidin-4-ylamino)piperidine-1-carboxylate (295 mg, 0.94 mmol) and 3-chloro-4-fluoroaniline (2.83 g, 19.4 mmol) was heated neat at 140° C. for 19 hours. Upon cooling, the melt was stirred in EtOAc and allowed to stand at room temperature for 1 hour. The precipitate was collected, washed with EtOAc and dried to give 256 mg (85%) of N4-(3-chloro-4-fluorophenyl)-N6-(piperidin-3-yl)pyrimidine-4,6-diamine, a grayish-violet amorphous solid. MS (APCI): (M+1)+=322.

Workup

  1. temperatureUpon cooling
  2. customThe precipitate was collected
  3. washwashed with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-433c3e8cd4f94fb787e778ae23883fd3
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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