Methanol → HCID 73855097, compound

HRID 2121931Notes

Reaction equation

HRID 2121931 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

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 3837531HCID 3837531, compound

Product 1

HCID 73855097HCID 73855097, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-c1db3e7ddfa54a90963d3e7d587119d3
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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