Disodium disulfite → HCID 25261021, compound

HRID 1966212Notes

Reaction equation

[C:1]1([S:7][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)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:28])C=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[C:1]1([S:7]([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:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(5-Phenylsulfanyl-pyridine-2-yl)-thiazole-2-yl-amine (0.13 mmol) is dissolved in dichloromethane, cooled to 0° C. and m-chloro-perbenzoic acid (1 eq.) is added. The reaction is stirred 30 min at 0° C. and 2.5 hours at RT. Sodium disulfite (50 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. “A13” is obtained after reversed phase column chromatography (water/acetonitrile) as a yellow powder in a yield of 44% HPLC (method C): 1.41 min; LC-MS (method A): 1.223 min, 301.95 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.657 (s, 1H), 8.634-8.628 (m, 1H), 7.853 (dd, 1H, J=2.4 Hz, J=8.9 Hz), 7.722-7.703 (m, 2H), 7.583-7.507 (m, 3H), 7.425 (d, 1H, J=3.6 Hz), 7.152 (d, 1H, J=8.9 Hz), 7.100 (d, 1H, J=3.6 Hz).

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“A13” is obtained after reversed phase column chromatography (water/acetonitrile) as a yellow powder in a yield of 44% HPLC (method C)
custom1.41 min
custom1.223 min, 301.95 (M+H+)

Sources & evidence

ORD record: ord-43d2010b2ece4fa3ae1bbd5a615ee0b7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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