Diisopropylethylamine → 4-amino-5-chloro-2-fluoro-N-(1-methyl-4-piperidyl)benzamide

HRID 2234447Notes

Reaction equation

HRID 2234447 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)C>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[O:8])=[C:4]([F:12])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686839334-Amino-5-chloro-2-fluorobenzoic acid2×

Product 1

HCID 686824664-amino-5-chloro-2-fluoro-N-(1-methyl-4-piperidyl)benzamideYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-amino-5-chloro-2-fluorobenzoic acid (Intermediate 176; 500 mg, 2.64 mmol), 4-amino-1-methylpiperidine (452 mg, 3.96 mmol) and diisopropylethylamine (1.38 ml, 7.91 mmol) were stirred in DMF (5 mL) and HATU (1.50 g, 3.96 mmol) added. The reaction mixture was stirred for 3 hours at room temperature. The mixture was absorbed on to an SCX column, which was washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated to give a crystalline solid that was suspended in diethyl ether and filtered to yield the title compound as a pale brown solid (572 mg, 76%).

Workup

  1. customThe mixture was absorbed on to an SCX column, which
  2. washwas washed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. concentrationwere concentrated
  6. customto give a crystalline solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ac8e82a012ec49d78983a198d8c28bf3
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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