Hydrochloric Acid → HCID 86696276, compound

HRID 2175152Notes

Reaction equation

HRID 2175152 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([S:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:19]4)=[N:13][N:14]=2)[CH:11]=1)=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[O:29]1[CH2:28][CH2:27][N:26]([C:20]2[CH:21]=[N:22][C:23]3[C:18]([CH:19]=2)=[CH:17][C:16]([S:15][C:12]2[N:10]4[CH:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]4=[N:14][N:13]=2)=[CH:25][CH:24]=3)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86696274HCID 86696274, compound

Product 1

HCID 86696276HCID 86696276, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude (77.2) was dissolved in THF (20 ml) and 1 ml of HCl (2N) was added. The mixture was stirred at rt for 10 min. The mixture was neutralized by saturated aqueous NaHCO3 and evaporated to dryness. The residue was purified by column chromatography (CombiFlash-ISCO, eluent DCM/MeOH from 20/1 to 8/1 for 40 min gradiently) to afford the title compound (40 mg, yield 39.8% over 2 steps). LCMS (method A): [M+H]+=405.6, tR=2.08 min. 1H NMR (400 MHz, CDCl3) δ ppm 2.57 (s., 3H) 3.17-3.34 (t, 4H) 3.82-4.00 (t, 4H) 7.15 (d, 1H) 7.46 (d, 1H) 7.64 (s, 1H) 7.88 (s, 2H) 7.93 (d, 1H) 8.76 (d, 1H) 8.78 (s, 1H)

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by column chromatography (CombiFlash-ISCO, eluent DCM/MeOH from 20/1 to 8/1 for 40 min gradiently)

Sources & evidence

ORD record
ord-8d786eaa7e0541e692ebf2f6b601f55f
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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