Disodium disulfite → HCID 25261020, compound

HRID 1966213Notes

Reaction equation

C1(S[C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[S:16][CH:17]=[CH:18][N:19]=3)=[N:12][CH:13]=2)C=CC=CC=1.Cl[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](C(OO)=O)[CH:22]=1.[S:31]([O:34]S([O-])=O)([O-])=[O:32].[Na+].[Na+]>ClCCl>[C:21]1([S:31]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[S:16][CH:17]=[CH:18][N:19]=3)=[N:12][CH:13]=2)(=[O:34])=[O:32])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(5-Phenylsulfanyl-pyridine-2-yl)-thiazole-2-yl-amine (0.07 mmol) is dissolved in dichloromethane, cooled to 0° C. and m-chloro-perbenzoic acid (3 eq.) is added. The reaction is stirred 30 min at 0° C. and 22 hours at RT. Sodium disulfite (40 ml) is added and extracted with dichloromethane. The combined organic layers are washed with saturated NaHCO3, dried over MgSO4 and the solvent is removed in vacuo. “A14” is obtained after reversed phase column chromatography (water/acetonitrile) as a colourless powder in a yield of 41%; HPLC (method C): 1.63 min; LC-MS (method A): 1.537 min, 317.95 (M+H+); 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 11.907 (s, 1H), 8.837-8.829 (m, 1H), 8.146 (dd, 1H, J=2.6 Hz, J=8.9 Hz), 8.006-7.976 (m, 2H), 7.714-7.671 (m, 1H), 7.645-7.605 (m, 2H), 7.456 (d, 1H, J=3.6 Hz), 7.185-7.154 (m, 2H).

Workup

extractionextracted with dichloromethane
washThe combined organic layers are washed with saturated NaHCO3
dry with materialdried over MgSO4
customthe solvent is removed in vacuo
custom“A14” is obtained after reversed phase column chromatography (water/acetonitrile) as a colourless powder in a yield of 41%
custom1.63 min
custom1.537 min, 317.95 (M+H+)

Sources & evidence

ORD record: ord-8cf6d2b03d644756b3dfc2f3c026685c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

Loading…