Hydrochloric Acid → HCID 71284828, compound

HRID 1481747Notes

Reaction equation

HRID 1481747 reaction equation
[CH2:1]([C:3]1[C:4]([OH:27])=[C:5]([C:23]([O:25]C)=[O:24])[C:6](=[O:22])[NH:7][C:8]=1[C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C:20](=O)[C:13]3=[CH:12][C:11]=2[CH:10]=1)[CH3:2].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Li+].[I-].Cl>ClCCCl.CC(O)=O>[CH2:1]([C:3]1[C:4]([OH:27])=[C:5]([C:23]([OH:25])=[O:24])[C:6](=[O:22])[NH:7][C:8]=1[C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][CH:20]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[C:13]3=[CH:12][C:11]=2[CH:10]=1)[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 66321Lithium iodideHCID 5049666Sodium triacetoxyborohydrideHCID 71284811HCID 71284811, compound

Product 1

HCID 71284828HCID 71284828, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 5-ethyl-4-hydroxy-2-oxo-6-(1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1,2-dihydropyridine-3-carboxylate (0.13 g, 0.37 mmol) in DCE (3 mL) was added pyrrolidine (60 μL, 0.8 mmol) and AcOH (30 μL). After stirring at room temperature for 1 h, NaBH(OAc)3 (0.17 g, 0.8 mmol) was added and stirred for an additional 1 h. The reaction mixture was then concentrated and to the crude residue was added H2O. The resulting precipitate was filtered and dried over N2 stream. The crude solid was dissolved in EtOAc (3 mL) and LiI (0.2 g, 1.6 mmol) was added. The resulting suspension was heated to 60° C. for 1 h. The reaction mixture was then cooled to room temperature and acidified with 4M HCl (1 mL). The resulting precipitate was filtered and rinsed with Et2O to afford the title compound as an orange solid (25 mg, 20%).

Workup

  1. stirringstirred for an additional 1 h
  2. concentrationThe reaction mixture was then concentrated and to the crude residue
  3. additionwas added H2O
  4. filtrationThe resulting precipitate was filtered
  5. dry with materialdried over N2 stream
  6. dissolutionThe crude solid was dissolved in EtOAc (3 mL)
  7. temperatureThe resulting suspension was heated to 60° C. for 1 h
  8. temperatureThe reaction mixture was then cooled to room temperature
  9. filtrationThe resulting precipitate was filtered
  10. washrinsed with Et2O

Sources & evidence

ORD record
ord-796c1d1d16b9411abee07fb7e019f85b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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