Hydrochloric Acid → (S)-3-(2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)-1-methylpiperidin-3-ol

HRID 1946095Notes

Reaction equation

Cl.[CH:2]([C:5]1[N:9]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([C:20]4([OH:26])[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]4)[N:16]3[CH3:19])=[C:12]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:11]=2)[C:8]2[CH:33]=[CH:34][CH:35]=[CH:36][C:7]=2[N:6]=1)([CH3:4])[CH3:3].[CH:37](I)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C.CN(C=O)C>[CH:2]([C:5]1[N:9]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([C@:20]4([OH:26])[CH2:25][CH2:24][CH2:23][N:22]([CH3:37])[CH2:21]4)[N:16]3[CH3:19])=[C:12]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[N:11]=2)[C:8]2[CH:33]=[CH:34][CH:35]=[CH:36][C:7]=2[N:6]=1)([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 75 °C

Procedure

The HCl salt of 3-(2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)piperidin-3-ol (80 mg) was reacted with isopropyl iodide (1.5 eq) and potassium carbonate (5 eq) in a 1:1 mixture of DMF and Acetonitrile (2 mL). The reaction was heated at 75° C. for 18 hours until complete. The reaction mixture was diluted with Ethyl acetate and extracted with a saturated ammonium chloride solution. The organic layer was dried, filtered and concentrated to give 581 [4.6 mg; MS (Q1) 491.3 (M)+] and 582 [4.7 mg; MS (Q1) 491.3 (M)+] following reverse phase purification and subsequent chiral separation.

Workup

extractionextracted with a saturated ammonium chloride solution
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-aac8ab3911bb4d1f9a40b5ab9a9ea407
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394796B2

Reaction notes

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