Water → 2,5,6-Trichloro-3-[N-(methoxycarbonylamino)iminomethylidene]-1-(beta-D-ribofuranosyl)indole

HRID 2076775Notes

Reaction equation

HRID 2076775 reaction equation
[Cl:1][C:2]1[N:3]([C@@H:15]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]2[OH:17])[C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][C:7]([Cl:13])=[C:6]([Cl:14])[CH:5]=2.[NH:24]([C:26]([O:28][CH3:29])=[O:27])[NH2:25].O>CO>[Cl:1][CH:2]1[C:10](=[C:11]=[N:25][NH:24][C:26]([O:28][CH3:29])=[O:27])[C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]1[C@@H:15]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]1[OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 80519Methyl carbazateHCID 3011610Ftcri

Product 1

HCID 865989702,5,6-Trichloro-3-[N-(methoxycarbonylamino)iminomethylidene]-1-(beta-D-ribofuranosyl)indoleYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5,6-Trichloro-3-formyl-1-(β-D-ribofuranosyl)indole (4.3, 122 mg, 0.32 mmol) was dissolved in MeOH (10 mL) to which was added methyl hydrazinocarboxylate (115 mg, 1.3 mmol). The resulting solution was heated on a 60 C oil bath for 16 h, then cooled to room temperature and poured into 100 mL of water, and the solvent evaporated to approx 50 mL. The resulting suspension was cooled to 4 C, then filtered and the solids rinsed with cold water (25 mL). The solids were recrystallized from boiling EtOAc/hexane to yield 123 mg (85%) of 4.31 as a pale pink crystalline solid: mp 217-219 C; Rf 0.2 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 11.17 (b, 1H, D2O exch.), 8.54 (s, 1H), 8.42 (s, 1H), 8.22 (b, 1H), 5.92 (d, 1H), 5.42-5.37 (m, 2H, D2O exch.), 5.25 (d, 1H, D2O exch.), 4.43 (q, 1H), 4.15 (d, 1H), 3.98 (d, 1H), 3.72 (b, 5H). 13C-NMR (125 MHz, DMSO-d6): δ 153.88, 133.17, 129.33, 126.08, 124.96, 124.06, 122.17, 115.34, 108.59, 88.76, 86.03, 71.30, 69.73, 69.62, 61.07, 52.04. HRMS (ES) m/z calcd. for C16H16Cl3N3O6.Na 474.0002, found 473.9999. Anal calcd for C16H16Cl3N3O6.¼ H2O: C, 42.03; H, 3.64; N, 9.19. Found: C, 42.11; H, 3.92; N, 9.18.

Workup

  1. temperatureThe resulting solution was heated on a 60 C oil bath for 16 h
  2. customthe solvent evaporated to approx 50 mL
  3. temperatureThe resulting suspension was cooled to 4 C
  4. filtrationfiltered
  5. washthe solids rinsed with cold water (25 mL)
  6. customThe solids were recrystallized

Sources & evidence

ORD record
ord-2926da75b7374496b4880f237a75aea7
Source dataset
uspto-grants-2011_04
Patent number
US07928080B2

Reaction notes

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