Hydrochloric Acid → HCID 86707734, compound

HRID 1190840Notes

Reaction equation

HRID 1190840 reaction equation
[C:1]1([C:7]2[CH:38]=[CH:37][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][C@H:21]([NH:32][S:33](=[O:36])(=[O:35])[NH2:34])[C:22]([O:24]CC5C=CC=CC=5)=O)=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].Cl>CO.C1COCC1>[C:1]1([C:7]2[CH:38]=[CH:37][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([CH2:20][C@@H:21]5[NH:32][S:33](=[O:35])(=[O:36])[NH:34][C:22]5=[O:24])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86707733HCID 86707733, compound

Product 1

HCID 86707734HCID 86707734, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 45b (130 mg, 0.24 mmol) in MeOH (3 mL) and THF (3 mL) at 0° C. was added a solution of NaOMe (1.0 M in MeOH, 0.11 mL, 0.48 mmol) and the reaction mixture was stirred for 0.5 h. The reaction mixture was added dropwise to 1 N HCl (5 mL) at 0° C. The solution was extracted with DCM (3×) then the combined extracts dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0 to 20% MeOH/DCM to give Compound 45c (51 mg, 46% yield) as a yellow solid. LCMS=1.80 min using analytical method (B), 442.0 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.44 (d, J=1.8 Hz, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.86-7.81 (m, 1H), 7.79-7.73 (m, 2H), 7.57-7.48 (m, 2H), 7.44-7.37 (m, 1H), 4.92 (s, 2H), 4.63 (dd, J=7.9, 4.6 Hz, 1H), 3.44-3.19 (m, 2H). LC/MS=1.80 min using analytical method (B), 442.0 (M+H).

Workup

  1. extractionThe solution was extracted with DCM (3×)
  2. dry with materialthe combined extracts dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0 to 20% MeOH/DCM

Sources & evidence

ORD record
ord-9b1c130977f149be91c3d28a3734b526
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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