Tetrahydrofuran → 3-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid (2-oxo-2-phenyl-ethyl)-amide

HRID 536131Notes

Reaction equation

HRID 536131 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21](O)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.Cl.C[N:36](C)[CH2:37][CH2:38]CN=C=NCC.C(N(CC)CC)C.[O:53]1CCCC1>>[O:53]=[C:38]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:37][NH:36][C:21]([C:10]1[N:11]=[C:12]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:13]2[C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:22]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574945353-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid

Product 1

HCID 593928943-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid (2-oxo-2-phenyl-ethyl)-amideYield 45%

Procedure

To a stirred solution of the product from Example 8.2 (324 mg, 1 mmol) in tetrahydrofuran (15 mL) at room temperature, was added the product from Example 12.1 (162 mg, 1.2 mmol), 1-hydroxybenzotriazole (162 mg, 1.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (191 mg, 1 mmol) and triethylamine (112 mg, 1.1 mmol) successively. After 3 h the reaction solution was quenched with of saturated aqueous sodium bicarbonate solution (5 mL). The mixture was extracted with ethyl acetate and the organic phase washed with water, brine then dried over (Na2SO4) and concentrated in vacuo. Flash chromatography of the residue afforded the desired product (215 mg, 45%).

Workup

  1. customAfter 3 h the reaction solution was quenched with of saturated aqueous sodium bicarbonate solution (5 mL)
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase washed with water, brine
  4. dry with materialthen dried over (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1cf80994fc0454498652d890a8aaf3b
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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