Pyridine → HCID 21875928, compound

HRID 1454610Notes

Reaction equation

HRID 1454610 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([NH2:24])[C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:25][CH3:26])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3].N1C=CC=CC=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([NH:24][S:34]([CH3:33])(=[O:36])=[O:35])[C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:25][CH3:26])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21875554HCID 21875554, compound

Product 1

HCID 21875928HCID 21875928, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-[4-(6-amino-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl propionate (step 4, 1.0 g, 3.0 mmol) and pyridine (280 mg, 3.5 mmol) in dichloromethane (18 mL) was added methanesulfonyl chloride (372 mg, 3.3 mmol) at 0° C., and the mixture was stirred at room temperature for 16 h. The reaction was quenched with water (10 mL), and the mixture was extracted with dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and concentrated. Purification by flash column chromatography on silica gel eluting with ethyl acetate (gradient elution from 1:1 to 1:2) afforded 890 mg (70%) of the title compound as an amber oil: 1H-NMR (CDCl3) δ 8.26 (1H, s), 7.43 (2H, d, J=8.4 Hz), 7.32 (2H, d, J=8.2 Hz), 7.00 (1H, br.s), 4.35 (2H, t, J=7.0 Hz), 3.03-3.01 (5H, m), 2.85 (2H, q, J=7.5 Hz), 2.75 (3H, s), 2.35 (2H, q, J=7.5 Hz), 1.30 (3H, t, J=7.5 Hz), 1.14 (3H, t, J=7.5 Hz).

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionthe mixture was extracted with dichloromethane (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel eluting with ethyl acetate (gradient elution from 1:1 to 1:2)

Sources & evidence

ORD record
ord-5d72879a60bd43e58acdd5b60f0214ba
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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