Hydrochloric Acid → HCID 131736547, compound

HRID 1479067Notes

Reaction equation

HRID 1479067 reaction equation
Cl.C([O:6][C:7]([N:9]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([N:24]2[CH2:38][C:27]3=[C:28]4[N:33]([N:34]=[C:26]3[CH2:25]2)[C:32]([CH3:35])=[C:31]([Cl:36])[C:30]([CH3:37])=[N:29]4)=[O:23])[CH2:10]1)=[O:8])(C)(C)C.O>O1CCOCC1>[CH:7]([OH:8])=[O:6].[Cl:36][C:31]1[C:30]([CH3:37])=[N:29][C:28]2[N:33]([N:34]=[C:26]3[CH2:25][N:24]([C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH:11]4[CH2:12][CH2:13][NH:9][CH2:10]4)=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131736549HCID 131736549, compound

Product 1

HCID 131736547HCID 131736547, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of HCl in 1,4-dioxane (1.5 mL; 5.99 mmol; 10 eq.) was added to a suspension of 3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (315 mg; 0.6 mmol; 1 eq.) in 1,4-dioxane (10 mL) followed by water (30 μL) and the resulting mixture was stirred at room temperature for 5 hours. After concentration in vacuo, the residue was partitioned between DCM and 1M NaOH and the aqueous layer was extracted with DCM. The combined organic phase was dried over sodium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (51 mg, 18%) as a white solid. HPLC (max plot) 97.4%, Rt 2.74 min. UPLC/MS: (MS+) 426.4 ([M+H]+).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was partitioned between DCM and 1M NaOH
  3. extractionthe aqueous layer was extracted with DCM
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by mass

Sources & evidence

ORD record
ord-260d409b25784d8ca0dcf483f6f19f8d
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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