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Diisopropylethylamine → 6-Trifluoromethyl-pyridine-2-carboxylic acid (6-chloro-pyrimidin-4-yl)-amide

HRID 1486748
Notes
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Reaction equation

HRID 1486748 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[N:16]=[C:15]([C:17](Cl)=[O:18])[CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:1][C:17]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:21])([F:9])[F:20])[N:16]=2)=[O:18])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2380124-Amino-6-chloropyrimidineHCID 378634686-(Trifluoromethyl)pyridine-2-carbonyl chloride

Product 1

HCID 867065656-Trifluoromethyl-pyridine-2-carboxylic acid (6-chloro-pyrimidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-6-chloropyrimidine (230 mg, 1.78 mmol) in DCM (15 mL) is added 6-(trifluoromethyl)picolinoyl chloride (276 mg, 1.78 mmol) and DIPEA (0.912 ml, 5.33 mmol). The mixture is stirred overnight at RT. The mixture is diluted with DCM (10 mL), washed with saturated NaHCO3 solution (25 mL). The organic layer is dried over MgSO4 and evaporated under reduced pressure. The residue is purified by prep HPLC E, delivering the title compound as a yellowish solid (102 mg, 19%); LC-MS A: tR=0.89 min; [M+H]+=302.92.

Workup

  1. washwashed with saturated NaHCO3 solution (25 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe residue is purified by prep HPLC E

Sources & evidence

ORD record
ord-f3c94b70ba224265b9b9cfd9841f7878
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428456B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes