HCID 86607508, compound → HCID 66861293, compound

HRID 2368720Notes

Reaction equation

HRID 2368720 reaction equation
C(O[C:6]([C:8]1[N:13]=[C:12](Br)[C:11]2[CH:15]=[C:16]([S:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:17][C:10]=2[C:9]=1[OH:25])=[O:7])CCC.C([O:30][C:31]([C:33]1C(O)=C2C=C(SC3C=CC=CC=3)SC2=C(Br)[N:38]=1)=[O:32])CCC>>[OH:25][C:9]1[C:10]2[S:17][C:16]([S:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][C:11]=2[CH:12]=[N:13][C:8]=1[C:6]([NH:38][CH2:33][C:31]([OH:32])=[O:30])=[O:7]

Participants

3

Reactant 2

HCID 86607508HCID 86607508, compoundHCID 86607509HCID 86607509, compound

Product 1

HCID 66861293HCID 66861293, compound

Procedure

The title compound was prepared from a mixture of 4-bromo-7-hydroxy-2-phenylsulfanyl-thieno[3,2-c]pyridine-6-carboxylic acid n-butyl ester and 7-bromo-4-hydroxy-2-phenylsulfanyl-thieno[2,3-c]pyridine-5-carboxylic acid n-butyl ester, example 17.b, under conditions analogous to experimental example 1.g. The products were purified by column chromatography eluting from silica gel with a gradient of 20-60% ethyl acetate in hexanes. Product A, (Lower Rf product); MS: (+) m/z 360.01 (M+1); Product B, (Higher Rf product); MS: (+) m/z 360.02 (M+1).

Workup

  1. customThe products were purified by column chromatography
  2. washeluting from silica gel with a gradient of 20-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d055e2bc00ec43a09b2307fc07fdcf29
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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