Acetic Anhydride → HCID 10392462, compound

HRID 373626Notes

Reaction equation

HRID 373626 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([OH:28])[CH2:17][S:18][C:19]3[N:27]=[CH:26][N:25]=[C:24]4[C:20]=3[NH:21][CH:22]=[N:23]4)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37].CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH:16]([O:28][C:36](=[O:38])[CH3:37])[CH2:17][S:18][C:19]3[N:27]=[CH:26][N:25]=[C:24]4[C:20]=3[NH:21][CH:22]=[N:23]4)[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 193951Carsatrin

Product 1

HCID 10392462HCID 10392462, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-[1-[1-[bis(4-fluorophenyl)methyl]-piperazin-4-yl]-2-hydroxy-3-propanylthio]purine (1.0 g, 0.002 mol) in CH2Cl2 (7 mL), acetic anhydride (0.2 mL, 0.002 mol) in Et3N (0.2 mL, 0.002 mol) was added dropwise over 5 min at room temperature under nitrogen. After 70 h, CH2Cl2 (50 mL) was added and the solution was extracted with saturated NaHCO3 (2×100 mL), H2O (1×100 mL), and saturated brine (1×100 mL); the organic layer was dried over Na2SO4. Solvent removal of the dried organic layer gave a solid which was dried in vacuo at 40° C. to give pure product (0.7 g, 64.8%), mp 105°-109° C. (dec). DCI/MS (M+1) 539. 400 MHz 1H NMR (CDCl3) δ: 8.7 (s, 1H), 8.2 (s, 1H), 7.3 (m, 4H), 6.95 (m, 4H), 5.3 (m, 1H), 4.2 (s, 1H), 3.4 and 4.0 (m, 2 H), 2.65 (m, 2H), 2.6 (m, 4H), 2.4 (m, 4H), 2.0 (s, 3H).

Workup

  1. extractionthe solution was extracted with saturated NaHCO3 (2×100 mL), H2O (1×100 mL), and saturated brine (1×100 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customSolvent removal of the dried organic layer
  4. customgave a solid which
  5. customwas dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-135d1e38b1d04dcd8b16fdb20949ff86
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

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