HCID 22868433, compound → HCID 53894413, compound

HRID 1082097Notes

Reaction equation

HRID 1082097 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][F:15])[O:7][C@H:6]1[N:16]1[C:31]2[N:30]=[C:29]([Cl:32])[N:28]=[C:20]([NH:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]=2[N:18]=[CH:17]1)(=O)C>N>[Cl:32][C:29]1[N:28]=[C:20]([NH:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:19]2[N:18]=[CH:17][N:16]([C:31]=2[N:30]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][F:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

3

Reactant 1

HCID 22868433HCID 22868433, compound

Product 1

HCID 53894413HCID 53894413, compoundYield 581.7%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The above 2',3'-di-O-acetyl-2-chloro-5'-deoxy-5'-fluoro-N-(1-piperidinyl)adenosine (0.38 g, 0.8 mmol) was dissolved in methanolic ammonia (15 ml) and stirred for 1 h. The reaction mixture was evaporated in vacuo and the resultant residue was purified by flash chromatography eluting with dichloromethane and 10% ammonia in ethanol (95:5) to afford 2-chloro-5'-deoxy-5'-fluoro-N-(1-piperidinyl)adenosine (1.8 g, 86%) as a white solid, m.p. 199°-201° C. 1H-NMR (400 MHz, DMSO-d6) δ1.35 (2H, br, piperidine C--H), 1.52 (4H, br, piperidine C--H), 2.80 (4H, br, piperidine C--H), 4.10 (1H, ddd, H-4'), 4.20 (1H, br, H-3'), 4.51 (1H, br, H-2'), 4.65 (2H, dd, H-5'a and H-5'b), 5.88 (1H, d, H-1'), 8.28 (1H, s, H-8). HPLC retention time 7.15 min. (gradient elution over 30 min.; 20-80% acetonitrile/0.1% TFA in water). C15H20ClFN6O3, 0.75H2O requires C, 45.2; H, 5.4; N, 21.1. Found: C, 45.2; H, 5.2; N, 20.8%.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe resultant residue was purified by flash chromatography
  3. washeluting with dichloromethane and 10% ammonia in ethanol (95:5)

Sources & evidence

ORD record
ord-62283fd8b1da4392bbf90a89edef374a
Source dataset
uspto-grants-1996_12
Patent number
US05589467

Reaction notes

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