Boron Trichloride → 3-(1,3-dihydroxypropan-2-yl)-N-(7-(2-fluoro-4-iodophenylamino)-6-methyl-5-oxo-3,5-dihydro-2H-oxazolo[3,2-a]pyridin-8-yl)cyclobutane-1-sulfonamide

HRID 1259408Notes

Reaction equation

HRID 1259408 reaction equation
C([O:8][CH2:9][CH:10]([CH:20]1[CH2:23][CH:22]([S:24]([NH:27][C:28]2[C:33]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([I:41])=[CH:37][C:36]=3[F:42])=[C:32]([CH3:43])[C:31](=[O:44])[N:30]3[CH2:45][CH2:46][O:47][C:29]=23)(=[O:26])=[O:25])[CH2:21]1)[CH2:11][O:12]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:8][CH2:9][CH:10]([CH:20]1[CH2:21][CH:22]([S:24]([NH:27][C:28]2[C:33]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([I:41])=[CH:37][C:36]=3[F:42])=[C:32]([CH3:43])[C:31](=[O:44])[N:30]3[CH2:45][CH2:46][O:47][C:29]=23)(=[O:26])=[O:25])[CH2:23]1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 67345136HCID 67345136, compound

Product 1

HCID 529343263-(1,3-dihydroxypropan-2-yl)-N-(7-(2-fluoro-4-iodophenylamino)-6-methyl-5-oxo-3,5-dihydro-2H-oxazolo[3,2-a]pyridin-8-yl)cyclobutane-1-sulfonamideYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1,3-Bis(benzyloxy)propan-2-yl)-N-(7-(2-fluoro-4-iodophenylamino)-6-methyl-5-oxo-3,5-dihydro-2H-oxazolo[3,2-a]pyridin-8-yl)cyclobutane-1-sulfonamide (0.3 g, 0.388 mmol) was reacted with 1M BCl3 (1.1 mL, 1.164 mmol) and DCM (10 mL) at 0° C. for 30 minutes to afford the crude product. Purification by column chromatography on silica gel (8% methanol in chloroform) afforded 60 mg of the product (26% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (8% methanol in chloroform)

Sources & evidence

ORD record
ord-7ce8a676cef94e46b6e0eeacc04a563b
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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