Boron Trichloride → 3-Hydroxy-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 1259381Notes

Reaction equation

HRID 1259381 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:28][CH:27]([O:29]CC3C=CC=CC=3)[CH2:26]2)(=[O:24])=[O:23])=[C:12]2[NH:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].B(Cl)(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:28][CH:27]([OH:29])[CH2:26]2)(=[O:23])=[O:24])=[C:12]2[NH:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 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]-amide

Product 1

HCID 529350173-Hydroxy-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 29.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (120 mg, 0.19 mmol) in DCM (3 mL) was reacted with 1M BCl3 (67 mg, 0.57 mmol) at 0° C. The resulting mixture was stirred at room temperature for 6 hours. Purification by column chromatography on silica gel (5% MeOH in CHCl3), followed by preparative HPLC afforded 30 mg of the product (29.4% yield).

Workup

  1. customPurification by column chromatography on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-887374bc665f4692b1a6e640c8041d85
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…