Hydrazine hydrate (1:1) → HCID 178509210, compound

HRID 28358Notes

Reaction equation

HRID 28358 reaction equation
Cl[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]2O)[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][C:7]([Cl:13])=[C:6]([Cl:14])[CH:5]=2.[OH2:24].[NH2:25][NH2:26]>O>[Cl:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[Cl:14])[N:3]([C@@H:15]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]1[OH:24])[C:2]1[NH:25][N:26]=[C:11]([NH2:12])[C:10]2=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 30125652,5,6-trichloro-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]indole-3-carbonitrile

Product 1

HCID 178509210HCID 178509210, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,5,6-Trichloro-3-cyano-1-(β-D-ribofuranosyl)indole (4.4, 102 mg, 0.27 mmol) was dissolved in hydrazine hydrate (2 mL), and the resulting solution was stirred at room temperature for 30 min. The suspension thus obtained was diluted with water (8 mL), cooled to 0 □C, and the suspension filtered and the solids rinsed with water. The solids were recrystallized from MeOH/H2O to yield 91 mg (90%) of 4.37 as a white crystalline solid: mp 198-201 □C; Rf 0.3 (20% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.68 (s, 1H, D2O exch.), 7.76 (s, 1H), 7.27 (s, 1H), 5.81 (d, 1H), 5.78 (b, 1H, D2O exch.), 5.31-5.28 (m, 2H, D2O exch.), 4.84 (s, 2H, D2O exch.), 4.27 (q, 1H), 4.07 (s, 1H), 4.00 (s, 1H), 3.68 (q, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 155.50, 131.99, 129.00, 123.60, 121.60, 116.91, 115.45, 111.96, 88.32, 85.95, 71.06, 69.95, 63.28, 60.78. HRMS (EI) m/z calcd. for C14H14Cl2N4O4 372.0392, found 372.0397. Anal calcd for C14H14Cl2N4O4·¼H2O: C, 44.52; H, 3.87; N, 14.83. Found: C, 44.63; H, 4.10; N, 14.72.

Workup

  1. customThe suspension thus obtained
  2. temperaturecooled to 0 □C
  3. filtrationthe suspension filtered
  4. washthe solids rinsed with water
  5. customThe solids were recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-a95d5bddf3a94afb9af8ae1bccd79c31
Source dataset
uspto-grants-2008_09
Patent number
US07419963B2

Reaction notes

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