4-Methylmorpholine → (3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide

HRID 874619Notes

Reaction equation

HRID 874619 reaction equation
[F:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.FC1C=CC=CC=1C([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([CH3:55])=[CH:48][C:49]3[S:53][CH:52]=[N:51][C:50]=3[CH:54]=2)=[CH:42][N:41]=1)=O.C([O-])(O)=O.[Na+].CC(=O)OCC>C(Cl)Cl>[F:11][C:7]1[CH:8]=[N:9][CH:10]=[C:2]([F:1])[C:3]=1[C:4]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([CH3:55])=[CH:48][C:49]3[S:53][CH:52]=[N:51][C:50]=3[CH:54]=2)=[CH:42][N:41]=1)=[O:6]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 201118793,5-Difluoroisonicotinic acidHCID 58487026(2-fluorophenyl)-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamideHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 58487342(3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamideYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3,5-difluoroisonicotinic acid (24 mg, 0.15 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT)(35 mg, 0.2 mmol) and 45 μl N-methyl morpholine in 2 ml DCM was stirred at r.t. for 1 h before addition of 5-(6-methylbenzothiazol-5-yl)-2-pyridylamine (55) (24 mg, 0.1 mmol). The resulting reaction mixture was stirred at r.t. for overnight then at 50° C. for 3 h. The reaction mixture was worked up with aq. NaHCO3/EA. Org. phase was washed with brine, concentrated, subjected to silica flash column chromatography to furnish 8.9 mg (3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide (58) as yellow semi-solid. (yield: 23.3%, purity>90%).

Workup

  1. customThe resulting reaction mixture
  2. waitat 50° C. for 3 h
  3. washphase was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d15e9f7bd0d643608da7d92865d8508d
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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