Hydrochloric Acid → HCID 59605968, compound

HRID 1923204Notes

Reaction equation

HRID 1923204 reaction equation
Cl.[Cl:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[C:8]([C:13]3([OH:19])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[N:9]2[CH3:12])=[C:5]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:4]=1.[CH:26](I)([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[C:8]([C:13]3([OH:19])[CH2:18][CH2:17][CH2:16][N:15]([CH:26]([CH3:28])[CH3:27])[CH2:14]3)[N:9]2[CH3:12])=[C:5]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[N:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 81531DiisopropylethylamineHCID 59605929HCID 59605929, compound

Product 1

HCID 59605968HCID 59605968, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

The HCl salt of 3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)piperidin-3-ol (70 mg) was reacted with isopropyl iodide (1.5 eq), cesium carbonate (2 eq) and DIPEA (3 eq) in DMF (1 mL). The reaction was heated at 50° C. for several 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 70 mg of crude 3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)-1-isopropylpiperidin-3-ol which was reacted with 2-ethyl benzimidazole via General Procedure I for Buchwald coupling to give 515 [7.6 mg; MS (Q1) 505.3 (M)+] and 518 [7.7 mg; MS (Q1) 505.2 (M)+] following reverse phase purification and subsequent chiral separation.

Workup

  1. extractionextracted with a saturated ammonium chloride solution
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74f17b153a524fa492f8fce9d04e9697
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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