Hydrochloric Acid → HCID 58721758, compound

HRID 1246823Notes

Reaction equation

HRID 1246823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.[CH3:31][CH:32]([NH2:34])[CH3:33].Cl.[C-:36]#[N:37].[Na+]>CO.O.CC(N)C.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:29][CH2:28][C:27]([NH:34][CH:32]([CH3:33])[CH3:31])([C:36]#[N:37])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 8929Sodium Cyanide2×HCID 21905841686345-96-0

Product 1

HCID 58721758HCID 58721758, compound

Reagents, catalysts & solvents 4

HCID 6363IsopropylamineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-piperidin-4-one 7A-96 (48 mg, 0.11 mmol) in methanol (0.4 ml) was cooled to 0° C. and then treated with 2-propylamine (15 μl, 0.15 mmol) and then concentrated aqueous HCl. After stirring 5 minutes, a solution of sodium cyanide (8.1 mg, 0.16 mmol) in water (0.4 ml) was added; the heterogeneous reaction was warmed to room temperature and then allowed to stir overnight. Tetrahydrofuran (0.4 ml) was then added to solubilize all reactants. Additional sodium cyanide (8 mg, 0.16 mmol) and 2-propylamine (3 drops) were added and stirred overnight. The reaction was filtered and then concentrated under reduced pressure to give title compound 22A-1 (27 mg, 48%) as a colorless solid: +ESI MS (M+1) 506.1; 1H NMR (400 MHz, CD2Cl2) δ 8.32 (s, 1H), 7.52 (d, J=7.9 Hz, 1H), 7.45–7.33 (m, 5H), 7.21 (d, J=8.7 Hz, 2H), 5.50 (v br s, 2H), 3.88 (v br s, 2H), 3.18 (septuplet, J=6.0 Hz, 1H), 2.16 (m, 2H), 1.82 (ddd, J=13.3, 10.4, 3.7 Hz, 2H), 1.16 (d, J=6.2 Hz, 6H).

Workup

  1. customthe heterogeneous reaction
  2. stirringto stir overnight
  3. stirringstirred overnight
  4. filtrationThe reaction was filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57db7719e0d3412e8d8d958ee1388516
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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