Methanol → 3-Benzyloxy-cyclobutanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-8-yl]-amide

HRID 1259380Notes

Reaction equation

HRID 1259380 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[C:19]2=[C:20]([NH:35][S:36]([CH:39]3[CH2:42][CH:41]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:40]3)(=[O:38])=[O:37])[C:21]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=3[F:34])=[C:22]([CH3:25])[C:23](=[O:24])[N:18]2[CH2:17][CH2:16]1)=O)(C)(C)C.CO>C(Cl)(Cl)Cl>[F:34][C:28]1[CH:29]=[C:30]([I:33])[CH:31]=[CH:32][C:27]=1[NH:26][C:21]1[C:20]([NH:35][S:36]([CH:39]2[CH2:42][CH:41]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:40]2)(=[O:38])=[O:37])=[C:19]2[NH:15][CH2:16][CH2:17][N:18]2[C:23](=[O:24])[C:22]=1[CH3:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 671934168-(3-Benzyloxy-cyclobutanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671942983-Benzyloxy-cyclobutanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-8-yl]-amideYield 55.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dioxane hydrochloride (3 mL) was added to 8-(3-benzyloxy-cyclobutanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (250 mg) and the resulting mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was concentrated; the concentrate was neutralized with NaHCO3 solution and extracted with ethylacetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated to afford 120 mg of the product (55.8% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-914b0bb5eef74e848ff3be73f0e0c2f0
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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