Hydrochloric Acid → HCID 58529437, compound

HRID 1972887Notes

Reaction equation

HRID 1972887 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[N:23]3[C:18]([C:19]([NH2:24])=[N:20][CH:21]=[N:22]3)=[C:17]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:29]=4)[CH:16]=2)=[O:14])[CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[NH2:24][C:19]1[C:18]2=[C:17]([C:25]3[CH:26]=[CH:27][C:28]4[C:32]([CH:33]=3)=[N:31][N:30]([CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:29]=4)[CH:16]=[C:15]([C:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[O:14])[N:23]2[N:22]=[CH:21][N:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58529515HCID 58529515, compound

Product 1

HCID 58529437HCID 58529437, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from Step 3 (0.51 g, 0.94 mmol) was dissolved in THF (15 mL) and HCl in dioxane (4N, 2.34 mL) was added. The mixture was stirred for 12 hours and then concentrated. The residue was suspended in EtOAc, sonicated for 10 min and the white solid was filtered. The solid was partitioned between NaHCO3 saturated solution and i-PrOH/CHCl3 (1:2) mixture. The organic layer was separated and washed with brine, dried over Na2SO4 filtered and concentrated to provide 320 mg (78%) of the title compound. 1H-NMR (CD3OD-d4) 8.41-8.39 (m, 1H), 8.05 (s, 1H), 7.87 (dd, 1H), 7.71-7.69 (m, 1H), 7.70 (s, 1H), 7.37-7.29, (m, 5 H), 7.24 (dd, 1 H), 5.67 (s, 1 H), 4.39-4.31 (m, 1 H), 3.28-3.21 (m, 2 H), 3.12-2.96 (m, 2 H), 2.25-2.07 (m, 2 H); LC-MS [M+H]+=438.4, RT=2.52 min.

Workup

  1. concentrationconcentrated
  2. customsonicated for 10 min
  3. filtrationthe white solid was filtered
  4. customThe solid was partitioned between NaHCO3 saturated solution and i-PrOH/CHCl3 (1:2) mixture
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-20ca446ff9574eab9c81ca9cf90f2d1c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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