6-Chloronicotinic acid → HCID 22993400, compound

HRID 1167763Notes

Reaction equation

HRID 1167763 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][O:45][C:46]1[C:51]2[N:52]=[C:53]([NH2:55])[S:54][C:50]=2[C:49]([N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)=[CH:48][CH:47]=1>C1COCC1.O1CCOCC1.CN(C=O)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:55][C:53]2[S:54][C:50]3[C:49]([N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)=[CH:48][CH:47]=[C:46]([O:45][CH3:44])[C:51]=3[N:52]=2)=[O:8])=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 792226-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

Product 1

HCID 22993400HCID 22993400, compoundYield 99.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1.89 g (7.54 mmol) 6-chloro-nicotinic acid in 20 ml THF were added 2.87 g (7.54 mmol) HATU and 1.28 ml (7.54 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 30 minutes. A solution of 2.00 g (7.54 mmol) 4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine in 20 ml dioxane and 4 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 350 ml water and the mixture stirred for 30 min. The resulting crystals were collected by filtration, washed with methanol and then with ether, and dried in vacuo to afford 3.03 g (99%) 6-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide as a yellow crystalline solid. ES-MS m/e (%): 429 (M{37Cl}+Na+, 15), 427 (M{35Cl}+Na+, 38). 407 (M{37Cl}+H+, 40), 405 (M{31Cl}+H+, 100)

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. stirringthe mixture stirred for 30 min
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with methanol
  6. dry with materialwith ether, and dried in vacuo

Sources & evidence

ORD record
ord-1afa525989e94031b6b2ba047e083cb0
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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