Boron tribromide → HCID 21886270, compound

HRID 723066Notes

Reaction equation

HRID 723066 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C[O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]([C:32]([NH2:34])=[NH:33])[S:28][C:29]=3[S:30][CH3:31])(=[O:24])=[O:23])[CH:17]=2)[CH:13]=[CH:14][CH:15]=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:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([C:25]3[CH:26]=[C:27]([C:32]([NH2:34])=[NH:33])[S:28][C:29]=3[S:30][CH3:31])(=[O:24])=[O:23])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 21886610HCID 21886610, compound

Product 1

HCID 21886270HCID 21886270, compoundYield 77%

Procedure

4-(3′-Methoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate (1.4 mg, 3.3 μmol, as prepared in Example 44) 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 1.0 mg (77%) of the title compound as a white solid. 1H-NMR (CD3OD): δ 8.33 (s, 1H), 8.23 (t, 1H, J=1.6 Hz), 7.98–8.01 (m, 1H), 7.92–7.95 (m, 1H), 7.68 (t, 1H, J=7.8 Hz), 7.31 (t, 1H, J=7.8 Hz), 7.05–7.12 (m, 2H), 6.84–6.87 (m, 1H), 2.74 (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-403e0220b02f46deae0b75392bcf3796
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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