3-(Benzyloxy)cyclobutane-1-sulfonyl chloride → 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

HRID 1259379Notes

Reaction equation

HRID 1259379 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH2:28])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([O:36][CH:37]1[CH2:40][CH:39]([S:41](Cl)(=[O:43])=[O:42])[CH2:38]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:41]([CH:39]3[CH2:40][CH:37]([O:36][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:38]3)(=[O:43])=[O:42])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 583805353-(Benzyloxy)cyclobutane-1-sulfonyl chlorideHCID 671938118-Amino-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 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 esterYield 49.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and workup as described for the preparation of Intermediate (I-5d), 8-Amino-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 (I-5c: 350 mg, 0.7 mmol) in pyridine (3 mL) was reacted with 3-benzyloxy-cyclobutanesulfonyl chloride (273 mg, 1.05 mmol) to afford the crude product. Purification by column chromatography on silica gel (80% ethylacetate in hexane) afforded 250 mg of the product (45.3% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-57849d159ab848f88f29af70b32b53a8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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