Acetic Anhydride → HCID 88124317, compound

HRID 1655851Notes

Reaction equation

HRID 1655851 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:9]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]([OH:29])[CH2:18][S:19][C:20]3[N:28]=[CH:27][N:26]=[C:25]4[C:21]=3[NH:22][CH:23]=[N:24]4)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38].CCN(CC)CC>C(Cl)Cl>[OH2:29].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[N:9]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]([O:29][C:37](=[O:39])[CH3:38])[CH2:18][S:19][C:20]3[N:28]=[CH:27][N:26]=[C:25]4[C:21]=3[NH:22][CH:23]=[N:24]4)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:9]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH:17]([O:29][C:37](=[O:39])[CH3:38])[CH2:18][S:19][C:20]3[N:28]=[CH:27][N:26]=[C:25]4[C:21]=3[NH:22][CH:23]=[N:24]4)[CH2:11][CH2:10]2)[C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19789541HCID 19789541, compound

Product 1

HCID 88124317HCID 88124317, compoundYield 204.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-[1-[1-[bis(4-fluorophenyl)methyl]homopiperazin-4-yl]-2-hydroxy-3-propanylthio]purine (0.26 g, 0.51 mmol) (the filtrate from above) in methylene chloride (2 mL) was added acetic anhydride (0.05 mL, 0.51 mmol) in Et3N (0.07 mL, 0.51 mmol) at room temperature under a nitrogen atmosphere. After three days, the solution was filtered and the filtrate extracted with aqueous saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and saturated brine (1×50 mL), and dried over Na2SO4. Evaporation of the solvent gave a white solid (390 mg). After several washings with pentane, the solid was dried in a vacuum oven for 4 days to give pure product (0.160 g, 56.8%) as a white solid, mp 88°-90° C. (dec). DCI/MS (M+1) 553; 300 MHZ1H NMR (CDCl3) δ: 8.7 (s, 1H), 8.1 (s, 1H), 7.3 (m, 4H), 6.95 (m, 4H), 5.3 (m, 1H), 4.1 and 3.45 (q of q, 2H), 2.6-2.8 (m, 10H), 2.0 (s, 3H), 1.75 (m, 2H).

Workup

  1. filtrationthe solution was filtered
  2. extractionthe filtrate extracted with aqueous saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and saturated brine (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-36c47351926848d089286294a8f2e085
Source dataset
uspto-grants-1993_10
Patent number
US05252569

Reaction notes

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