Water → HCID 10041513, compound

HRID 1293474Notes

Reaction equation

HRID 1293474 reaction equation
N[C:2]1[CH:7]=[CH:6]N=C[CH:3]=1.Cl.C(N=[C:12]=[N:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])CC)C.C([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.[OH2:29].CN([CH:33]=[O:34])C>CN(C1C=CN=CC=1)C>[N:17]1[CH:16]=[CH:15][C:14]([NH:13][C:12]([C:3]2[C:28]3[C:26]4[C:25](=[CH:6][CH:7]=[CH:2][CH:3]=4)[NH:24][C:27]=3[C:6]([O:34][CH3:33])=[CH:7][CH:2]=2)=[O:29])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 962WaterHCID 17274-AminopyridineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 10041513HCID 10041513, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a stirred solution of intermediate 72 (0.1 gm, 0.4145 mmoles) in dry DMF (5 ml) at room temperature, 4-aminopyridine (0.043 gm, 0.456 moles) was added followed by N-ethyl N′-diethylaminopropyl carbodiimide HCl (0.104 gm, 0.539 mmoles) and DMAP (5.0 mg, 0.04 mmoles).To the above solution triethylamine (0.08 ml, 0.58 mmoles) was added and the reaction mixture was stirred at the same temperature for 15 hours. The reaction mixture was poured in to water (20 ml) and extracted with ethyl acetate (2×20 ml). The organic layer was washed with water (3×20 ml) followed by brine (15 ml), dried over Na2SO4 and concentrated to give 0.1 gm of crude material which was purified by column chromatography, to give 20 mg of the title compound as pale yellow solid, m. p: >250° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe organic layer was washed with water (3×20 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give 0.1 gm of crude material which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-853a2216d084443fa2bac014d4799e67
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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