Nicotinic Acid → HCID 57599804, compound

HRID 1787566Notes

Reaction equation

HRID 1787566 reaction equation
Br.[N:2]1[CH:3]=[CH:4][N:5]2[C:14]=1[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:7]=[C:6]2[NH2:15].[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[N:2]1[CH:3]=[CH:4][N:5]2[C:14]=1[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:7]=[C:6]2[NH:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 66594113677341-61-6

Product 1

HCID 57599804HCID 57599804, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of imidazo[1,2-c]quinazolin-5-amine hydrobromide (93 mg, 0.35 mmol) and nicotinic acid (124 mg, 1.01 mmol) and DMF (2.5 ml) at room temperature was added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (525 mg, 1.01 mmol) followed by N,N-diisopropylethyl amine (0.264 ml, 1.51 mmol), and the mixture was stirred at 80. for 6 hours. After cooling to room temperature, the reaction mixture was poured into aqueous saturated NaHCO3 solution. The resulting precipitate was collected by filtration, washed with acetone, and dried under reduced pressure to give N-imidazo[1,2-c]quinazolin-5-ylnicotinamide (40 mg, 39% yield) as a white solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with acetone
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0673f2d150e94a16ba8313c89eab5b8a
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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