Sodium Bicarbonate → HCID 57663751, compound

HRID 551107Notes

Reaction equation

HRID 551107 reaction equation
[Cl-].C(O[C:5](=[NH2+:22])[CH2:6][N:7]1[C:17]2[C:18]3[N:9]([CH2:10][C:11](=[O:20])[N:12]([CH3:19])[C:13]=3[CH:14]=[CH:15][CH:16]=2)[C:8]1=[O:21])C.N[CH2:24][CH2:25][C:26]1[CH:27]=[C:28]2[C:41](=[CH:42][C:43]=1[N+:44]([O-])=O)[CH2:40][C@:30]1([C:38]3[C:33](=[N:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]1=[O:39])[CH2:29]2.C([O-])(O)=O.[Na+]>CCO>[CH3:19][N:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[N:7]([CH2:6][C:5]4[NH:44][C:43]5[CH:42]=[C:41]6[C:28](=[CH:27][C:26]=5[CH2:25][CH2:24][N:22]=4)[CH2:29][C@@:30]4([C:38]5[C:33](=[N:34][CH:35]=[CH:36][CH:37]=5)[NH:32][C:31]4=[O:39])[CH2:40]6)[C:8](=[O:21])[N:9]([C:18]=23)[CH2:10][C:11]1=[O:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67172944HCID 67172944, compound2×HCID 67173624HCID 67173624, compound

Product 1

HCID 57663751HCID 57663751, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-ethoxy-2-(6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)ethaniminium chloride from Step B (72 mg, 0.22 mmol) and (2S)-5-(2-aminoethyl)-6-nitro-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (73 mg, 0.25 mmol, described in Intermediate 15) in EtOH (7 mL) was heated to 100° C. for 5 min then allowed to cool. The reaction was poured into dilute aqueous NaHCO3 (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 80:20, to give the title compound. MS: 71/Z=520 (M+1) HRMS: m/z=520.2081; calculated m/z=520.2092 for C29H26N7O3.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-c1512c335f2e4aa3b9633b55d04a29c4
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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