Water → HCID 58763579, compound

HRID 858899Notes

Reaction equation

HRID 858899 reaction equation
CO[C:3](=[O:25])[CH:4]([C:8]1[N:12]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[CH2:5][CH:6]=O.[CH3:26][NH2:27].[BH4-].[Na+].O>CO.CO.CCOC(C)=O>[CH3:26][N:27]1[CH2:6][CH2:5][CH:4]([C:8]2[N:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:3]1=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 58763581HCID 58763581, compound

Product 1

HCID 58763579HCID 58763579, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a magnetically stirred solution of 2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-4-oxo-butyric acid methyl ester 36b (0.035 g, 0.0988 mmol) in methanol (1 mL) at room temperature under Ar atmosphere was added a 40% aqueous solution of methyl amine (0.009 mL, 0.0988 mmol). The reaction mixture was stirred for 1 h at room temperature. NaBH4 (0.0074 g, 0.197 mmol) was added at room temperature. After 30 min, water (30 mL) was added, and the aqueous phase was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), and concentrated in vacuo to the crude product. The pure product was obtained by column chromatography over silica gel (EtOAc, then 4:96 MeOH/EtOAc as eluent), which gave the title compound (0.006 g, 19%) as a white solid. (400 MHz, CDCl3) 2.31 (s, 3H), 2.33 (m, 2H), 2.39 (s, 3H), 3.00 (s, 3H), 3.51 (m, 2H), 4.41 (t, J=10.2 Hz, 1H), 7.02 (dd, J=1.1, 9.1 Hz, 1H), 7.24 (d, J=7.7 Hz, 2H), 7.25 (s, 1H), 7.53 (m, 3H).

Workup

  1. waitAfter 30 min
  2. extractionthe aqueous phase was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo to the crude product
  5. customThe pure product was obtained by column chromatography over silica gel (EtOAc

Sources & evidence

ORD record
ord-f093d18b12fb4a7c89c18eaef057c1d0
Source dataset
uspto-grants-2006_12
Patent number
US07148353B2

Reaction notes

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