Nicotinic Acid → HCID 60205309, compound

HRID 1034675Notes

Reaction equation

HRID 1034675 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]2[NH:19][CH:20]=[C:21]([NH2:22])[C:10]=12.[C:23](O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.O>[Cl:8][C:9]1[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][N:12]=[C:11]2[NH:19][CH:20]=[C:21]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=3)[C:10]=12

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602053084-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205309HCID 60205309, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (“TEA”; 0.50 mL, 3.61 mmol) was added to 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.17 g, 0.72 mmol), nicotinic acid (0.18 g, 1.44 mmol) and BOP—Cl (0.37 g, 1.44 mmol) in DCM (10 mL). The mixture was stirred for 30 minutes, and water was added (10 mL). The solid formed was collected by filtration, washed with DCM (10 mL) and dried to give N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (80 mg, 0.2 mmol, 32% yield) as a solid.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with DCM (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-d9a967221dbb4ee2ad95623000e629b4
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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