Ethanethiol → HCID 52934095, compound

HRID 1259395Notes

Reaction equation

HRID 1259395 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[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].B(F)(F)F.CCOCC.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[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 58380571HCID 58380571, compound

Product 1

HCID 52934095HCID 52934095, compoundYield 26%

Procedure

Using the same reaction conditions and workup as described for the prepaqration of Example 7A, 1-benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.27 g, 0.515 mmol) was reacted with BF3.OEt2(1.94 mL, 15.45 mmol) and ethane thiol (0.3 g, 5.15 mmol). The resulting mixture was stirred at room temperature for 3 days. Purification by preparative HPLC afforded 60 mg of the product (26% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-eae1c6194ce84af78cd6c9a3ccc2fbd8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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