Ethanethiol → HCID 52934559, compound

HRID 1259425Notes

Reaction equation

HRID 1259425 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]([C:25]2([CH2:28][O:29]CC3C=CC=CC=3)[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:12]2[S:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].C(S)C>>[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]([C:25]2([CH2:28][OH:29])[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:12]2[S:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

Participants

3

Reactant 2

HCID 6343EthanethiolHCID 58380550HCID 58380550, compound

Product 1

HCID 52934559HCID 52934559, compoundYield 56.5%

Conditions

Temperature
40 °C

Procedure

Using the same reaction conditions and workup as described for the preparation of Example 21A, 1-benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-amide (0.2 g, 0.321 mmol) was reacted with BF3OEt2(0.79 mL, 6.24 mmol) and ethane thiol (0.2 mL, 3.21 mmol). The resulting mixture was stirred at 40° C. for 6 hours. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 100 mg of the product (55% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-6aeb10d7fb76484787b9e4cc0233fe3c
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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