HCID 86629744, compound → HCID 57663767, compound

HRID 551100Notes

Reaction equation

HRID 551100 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]([CH2:37][C:38]([O:40]C)=O)[C:11](=[O:36])[N:12]([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)[NH:27][C:26]6=[O:34])[CH2:24][C:19]=5[CH:20]=4)[N:15]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.[Fe]>[O:34]=[C:26]1[NH:27][C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:33]2[C@:25]21[CH2:24][C:19]1[CH:20]=[C:21]3[C:16](=[CH:17][C:18]=1[CH2:35]2)[N:15]=[C:14]([CH2:13][N:12]1[C:8]2[C:9]4[N:10]([CH2:37][C:38](=[O:40])[NH:1][C:4]=4[CH:5]=[CH:6][CH:7]=2)[C:11]1=[O:36])[CH:23]=[CH:22]3

Participants

4

Reactant 1

HCID 86629744HCID 86629744, compound

Product 1

HCID 57663767HCID 57663767, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst3×HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl (7-nitro-2-oxo-3-{[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step A (55 mg, 0.100 mmol) and iron powder (15 mg, 0.269 mmol) was heated to 80° C. in AcOH (1 mL) for 2 h. Iron powder (15 mg, 0.269 mmol) was added and the mixture was heated to 80° C. for 1 h, then more iron powder (15 mg, 0.269 mmol) was added and the mixture was heated to 100° C. for 1 h. The cooled mixture was filtered then partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (20 mL). The organic layer was removed and the aqueous layer was extracted further with CH2Cl2 (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and 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=489 (M+1). HS: m/z=489.1662; calculated m/z=489.1670 for C28H21N6O3.

Workup

  1. temperaturethe mixture was heated to 100° C. for 1 h
  2. filtrationThe cooled mixture was filtered
  3. customthen partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (20 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted further with CH2Cl2 (2×20 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by HPLC
  10. washeluting with a gradient of H2O
  11. additionThe pure, product-containing fractions
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-448c5dd37fd842d18cebe1afbe29b07b
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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