Hydrochloric Acid → HCID 86761317, compound

HRID 551101Notes

Reaction equation

HRID 551101 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:36][C:37]([O:39]C)=O)=[CH:7][N:8]2[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][C:18]3[CH2:35][C@:25]4([C:33]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[NH:27][C:26]4=O)[CH2:24][C:19]=3[CH:20]=2)[N:15]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>O.CCO>[O:39]=[C:37]1[CH2:36][C:6]2=[CH:7][N:8]([CH2:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][C:18]5[CH2:35][C@:25]6([C:33]7[C:28](=[N:29][CH:30]=[CH:31][CH:32]=7)[N:27]=[CH:26]6)[CH2:24][C:19]=5[CH:20]=4)[N:15]=3)[C:9]3[C:5]2=[C:4]([CH:12]=[CH:11][CH:10]=3)[NH:1]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium Dithionite2×HCID 86761318HCID 86761318, compound

Product 1

HCID 86761317HCID 86761317, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of methyl (4-nitro-1-{[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-1H-indol-3-yl)acetate from Step A (22 mg, 0.041 mmol) in H2O (0.5 mL) and EtOH (0.5 mL) was added sodium hydrosulfite (ca. 85%; 108 mg, 0.53 mmol). The reaction mixture was stirred at ambient temperature for 1 h, then at 50° C. for 90 min. The reaction mixture was allowed to cool, more sodium hydrosulfite (ca. 85%; 55 mg, 0.27 mmol) was added, and the resulting mixture was heated to 70° C. for 4 h. 3 N hydrochloric acid (0.55 mL, 1.65 mmol) was added and the solution was heated to 70° C. for 18 h. EtOH (1 mL) was added and heating was continued at 100° C. for 24 h, then the cooled mixture was concentrated in vacuo. The residue was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=472 (M+1). HRMS: m/z=472.1764; calculated m/z=472.1768 for C29H22N5O2.

Workup

  1. waitat 50° C. for 90 min
  2. temperatureto cool
  3. temperaturethe resulting mixture was heated to 70° C. for 4 h
  4. temperaturethe solution was heated to 70° C. for 18 h
  5. temperatureheating
  6. waitwas continued at 100° C. for 24 h
  7. concentrationthe cooled mixture was concentrated in vacuo
  8. customThe residue was purified by HPLC
  9. washeluting with a gradient of H2O
  10. additionThe pure, product-containing fractions
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-4a14051bf6974e2190e07c7a75ce5764
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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