Methanol → HCID 73855097, compound

HRID 1241957Notes

Reaction equation

[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([O:24]C)[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[NH:35][CH2:36][CH3:37])[C:30]#[N:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([OH:24])[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[NH:35][CH2:36][CH3:37])[C:30]#[N:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of the product of Example 56 (1.06 g, 2 mmol) in DCM (10 mL) was added BBr3 (1.0 M in DCM, 2 mL) dropwise at −78° C. It was warmed to 20° C. slowly and the suspension was stirred for 72 h at 20° C. under N2. MeOH was added to decompose BBr3 at 0° C. Solvent was removed to give a crude, which was purified by chromatography on silica gel eluting with MeOH-DCM (2.5:97.5) to afford the title compound (0.6 g). 1H-NMR indicated one isomer. 1H-NMR (DMSO-d6): δ 9.66 (1H, s), 7.35 (1H, d), 7.13–7.24 (5H, m), 6.99 (1H, d), 6.60 (1H, d), 6.53 (1H, dd), 6.46 (1H, d), 4.96 (2H, s), 4.82(1H, t), 3.58 (3H, s), 2.89 (2H, m), 0.84 (3H, t); MS (ESI): 514 (MH+).

Workup

customat 0° C
customSolvent was removed
customto give a crude, which
customwas purified by chromatography on silica gel eluting with MeOH-DCM (2.5:97.5)

Sources & evidence

ORD record: ord-1d28f31f65cd4c1ba9dd34271efad945
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115640B2

Reaction notes

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