Ethanethiol → HCID 67418061, compound

HRID 1056910Notes

Reaction equation

HRID 1056910 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]2[C:24]3[N:23]=[CH:22][N:21]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])[C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH:10]=1)C1C=CC=CC=1.C(S)C.B(F)(F)F>C(Cl)Cl.CO>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:21]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([N:11]3[CH:12]=[CH:13][C:14](=[O:15])[C:9]([OH:8])=[CH:10]3)[C:24]=2[N:23]=[CH:22]1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 6356Boron trifluorideHCID 67419350HCID 67419350, compound

Product 1

HCID 67418061HCID 67418061, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzyloxy)-1-[1-(2-chlorobenzyl)-1H-benzimidazol-4-yl]pyridin-4(1H)-one (2.6 g, 5.9 mmol) in DCM (40 mL) was added ethanethioi (4 mL) and BF3 Et20 (4 mL) and the mixture was stirred at r.t. for 4 h. The mixture was diluted with MeOH, stirred for 10 min, then concentrated. The residue obtained was purified by prep-HPLC to give 1.2 g (58%) of 1-[1-(2-chlorobenzyl)-1H-benzimidazol-4-yl]-3-hydroxypyridin-4(1H)-one. ′H-NMR (CD3OD, 400 MHz) δ 8.48-8.44 (m, 3H), 7.78 (d, J−7.6 Hz, 1H), 7.58-7.51 (m, 3H), 7.41-7.25 (m, 4H), 5.75 (s, 2H). MS (ESI) (M+H 352.1/354.1.

Workup

  1. stirringstirred for 10 min
  2. concentrationconcentrated
  3. customThe residue obtained
  4. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-59d0bc22b67b424494360a51927f228c
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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