Dichloromethane → HCID 10202174, compound

HRID 1432375Notes

Reaction equation

HRID 1432375 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][CH2:21][CH2:20]3)[N:3]=1.Cl.[OH:27][CH:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>N1C=C(C)C=CC=1C>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([N:30]2[CH2:31][CH2:32][CH2:33][CH:28]([OH:27])[CH2:29]2)=[N:3][C:4]=3[NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][CH2:21][CH2:20]3)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2723962Piperidine-3-ol hydrochlorideHCID 17954015HCID 17954015, compound

Product 1

HCID 10202174HCID 10202174, compound

Reagents, catalysts & solvents 1

HCID 115262,5-DimethylpyridineSolvent

Conditions

Temperature
180 °C

Procedure

(2-Chloro-9-cyclopentyl-9H-purin-6-yl)-indan-5-yl-amine (283 mg, 0.8 mmol), 3-hydroxypiperidine hydrochloride (550 mg, 4 mmol) and K2CO3 (829 mg, 6 mmol) were suspended in 2,5-lutidine (10 mL) and the mixture was heated at 180° C. for 4 h. After cooling, CH2Cl2 (50 mL) was added and the solution was extracted with brine (2×15 mL). The organic fraction was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (95:5 CH2Cl2/MeOH) to afford the title compound as a slightly yellow foam (320 mg, 95.6%). Anal. RP-HPLC (Phenomenex Jupiter, 5 μ, C18, 300 Å, 4.6×250 mm; 1 mL/min): tR=19.6 min (10-70% MeCN in 0.1% aq CF3COOH over 20 min); tR=15.4 min (40-50% MeCN in 0.1% aq CF3COOH over 20 min); purity>92% (λ=214 nm). DE-MALDI-TOF MS: [M+H]+=419.5 (C24H30N6O=418.5).

Workup

  1. temperatureAfter cooling
  2. extractionthe solution was extracted with brine (2×15 mL)
  3. dry with materialThe organic fraction was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-57520011ac8a4cceb346497b99b31764
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

Loading…