Hydrochloric Acid → HCID 136365461, compound

HRID 419767Notes

Reaction equation

HRID 419767 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[C:12](=[C:14]([C:18]([NH2:20])=[O:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]3[C:12](=[C:14]([C:18]([NH2:20])=[O:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 66651303HCID 66651303, compound

Product 1

HCID 136365461HCID 136365461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of EXAMPLE 1E (0.55 g) and a 1M solution of boron tribromide in dichloromethane (25.1 mL) were stirred at ambient temperature for 3 hours. The mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The precipitate that formed in the aqueous phase was filtered to afford the title compound. 1H NMR (DMSO-d6) δ 10.35 (s, 1H), 9.27 (s, 1H), 8.30 (d, J=6.7 Hz, 1H), 8.17 (d, J=6.7 Hz, 1H), 8.00-8.03 (m, 2H), 8.92 (s, 1H), 7.53 (t, J=7.9 Hz, 1H), 6.95-6.99 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe precipitate that formed in the aqueous phase
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-a912a779014443dab69a743ed02e4c23
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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