Boron tribromide → HCID 21886340, compound

HRID 723065Notes

Reaction equation

HRID 723065 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([C:25]2[CH:26]=[C:27]([C:32]([NH2:34])=[NH:33])[S:28][C:29]=2[S:30][CH3:31])(=[O:24])=[O:23])[CH:17]=1.B(Br)(Br)Br>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([C:25]2[CH:26]=[C:27]([C:32]([NH2:34])=[NH:33])[S:28][C:29]=2[S:30][CH3:31])(=[O:24])=[O:23])[CH:17]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 21886315HCID 21886315, compound

Product 1

HCID 21886340HCID 21886340, compoundYield 77%

Procedure

4-(2′-Methoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate (46 mg, 0.086 mmol, as prepared in Example 34, step a) was treated with BBr3 (1 M in DCM) for 18 hr at rt. The reaction was quenched with MeOH at 0° C. and then concentrated in vacuo to a solid. Purification of this solid using C18-HPLC (10–80% CH3CN in H2O (0.1% TFA) over 25 min) afforded 34 mg (77%) of the title compound as a white solid. 1H-NMR (CD3OD): δ 8.30 (s, 1H), 8.27 (t, 1H, J=1.9 Hz), 7.89–7.96 (m, 2H), 7.61 (t, 1H, J=7.9 Hz), 7.26–7.30 (m, 1H), 7.19–7.24 (m, 1H), 6.90–6.95 (m, 2H), 2.70 (s, 3H). ESI-MS (m/z): Calcd. for C18H16N2O3S3: 405.5 (M+H); found: 405.2.

Workup

  1. customThe reaction was quenched with MeOH at 0° C.
  2. concentrationconcentrated in vacuo to a solid
  3. customPurification of this solid
  4. custom(10–80% CH3CN in H2O (0.1% TFA) over 25 min)

Sources & evidence

ORD record
ord-b881ad72d9d94d25be5a049e80b5a7a0
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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