Methanol → HCID 16729174, compound

HRID 1348575Notes

Reaction equation

HRID 1348575 reaction equation
C([O:8][CH2:9][CH:10]([O:20][CH2:21][N:22]1[CH:29]=[C:28]([I:30])[C:26](=[O:27])[NH:25][C:23]1=[O:24])[CH2:11][O:12]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO.[NH4+].[OH-]>C(Cl)Cl>[OH:12][CH2:11][CH:10]([O:20][CH2:21][N:22]1[CH:29]=[C:28]([I:30])[C:26](=[O:27])[NH:25][C:23]1=[O:24])[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 68632338HCID 68632338, compound

Product 1

HCID 16729174HCID 16729174, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 45 (1.90 g, 3.64 mmol) in anhydrous CH2Cl2 (60 mL) at −78° C. was added BCl3 (1 M solution in CH2Cl2, 30 mL, 30 mmol) dropwise. The mixture was stirred at −78° C. under nitrogen for 2 h, then at −60° C. for another 4 h. MeOH (10 mL) was added to quench the reaction, followed by 14% NH4OH solution to adjust the mixture to pH 7. After being stirred at room temperature for 1 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (9:1 to 4:1) to give the title compound 46 as a pale yellow solid (810 mg, 65%). 1NMR (DMSO-d6) δ 11.6 (s, 1H, NH), 8.19 (s, 1H, H-6), 7.20, 6.60 (2br, 2H, 2 OH), 5.15 (s, 2H, CH2N), 4.60 (m, 2H, CH2O), 3.53 (m, 1H, CHO), 3.41 (m, 2H, 2 CH2O).

Workup

  1. waitat −60° C. for another 4 h
  2. customto quench
  3. customthe reaction
  4. stirringAfter being stirred at room temperature for 1 h
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (9:1 to 4:1)

Sources & evidence

ORD record
ord-18b23bfcd6a04029a9f58b94e3c24219
Source dataset
uspto-grants-2007_05
Patent number
US07211570B2

Reaction notes

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