Methanol → HCID 66635144, compound

HRID 510108Notes

Reaction equation

HRID 510108 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:14])OCCCl)=[C:6]([NH2:15])[N:5]=[C:4]([N:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])=[N:17]2)[N:3]=1.[CH3:33][O-:34].[Na+].[CH3:36]O>>[NH2:1][C:2]1[N:3]=[C:4]([N:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])=[N:17]2)[N:5]=[C:6]2[C:7]=1[N:8]([CH2:36][CH2:33][OH:34])[C:9](=[O:14])[NH:15]2

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 66635088HCID 66635088, compound

Product 1

HCID 66635144HCID 66635144, compound

Conditions

Temperature
65 °C

Procedure

120 mg (0.263 mmol) of the carbamate from example 51A were initially charged in methanol (5.0 ml), 100 μl (0.525 mmol) of sodium methoxide solution (25% w/w in methanol) were added and the mixture was stirred at 65° C. for 30 min. The solvent was removed under reduced pressure, the residue was separated by means of preparative HPLC and the product fractions were concentrated. This gave 53.1 mg (48% of theory) of the title compound in solid form.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was separated by means of preparative HPLC
  3. concentrationthe product fractions were concentrated

Sources & evidence

ORD record
ord-cda97d49ce404a6abcc884abd7a88986
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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