Acetyl chloride → HCID 18336831, compound

HRID 2297689Notes

Reaction equation

[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@@H:20]3[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@H:19]3[C@@H:18]([C:26]([NH:28][NH2:29])=[O:27])[O:17]2)=[C:4]([F:32])[CH:3]=1.C(N(C(C)C)CC)(C)C.[C:42](Cl)(=[O:44])[CH3:43]>CN(C=O)C>[C:42]([NH:29][NH:28][C:26]([C@@H:18]1[C@H:19]2[C@@H:20]([O:21][C:22]([CH3:24])([CH3:25])[O:23]2)[C@H:16]([N:11]2[CH:10]=[N:9][C:8]3[C:12]2=[N:13][CH:14]=[N:15][C:7]=3[NH:6][C:5]2[CH:30]=[CH:31][C:2]([Cl:1])=[CH:3][C:4]=2[F:32])[O:17]1)=[O:27])(=[O:44])[CH3:43]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (3aR,4S,6R,6aR)-6-[6-(4-chloro-2-fluoroanilino)-9H-purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole4-carbohydrazide (50 mg) in N,N′-dimethylformamide (2 ml) at 0° C. was added diisopropylethylamine (28 μl) and acetyl chloride (9 mg). The reaction mixture was stirred at 0 ° C. for 5 h. The mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was washed with brine (20 ml), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by automated preparative HPLC (gradient profile 5-95% (ii) over 18.5 min) to give the title compound (25 mg).

Workup

customThe mixture was partitioned between ethyl acetate (20 ml) and water (20 ml)
washThe organic layer was washed with brine (20 ml)
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customThe residue was purified by automated preparative HPLC (gradient profile 5-95% (ii) over 18.5 min)

Sources & evidence

ORD record: ord-08a3837bd1ac4766bda16464efbf92eb
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492348B1

Reaction notes

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