Ethanol, reaction products with ammonia, distn. residues → HCID 22133919, compound

HRID 1826533Notes

Reaction equation

HRID 1826533 reaction equation
Cl[C:2]1[N:10]=[C:9]([C:11]#[C:12][C:13]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)[N:6]2[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24].[NH3:35].C(O)C>>[NH2:35][C:2]1[N:10]=[C:9]([C:11]#[C:12][CH:13]([OH:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)[N:6]2[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24]

Participants

3

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 22133740HCID 22133740, compound

Product 1

HCID 22133919HCID 22133919, compoundYield 73%

Procedure

3-{6-Chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl}-9H-9-purinyl]benzonitrile (2.0 g) was suspended in 200 ml of a 20% ammonia/ethanol and reacted at 100° C. in an autoclave for 8 hours. The resulting mixture was cooled to room temperature, concentrated to dryness and purified by a silica gel column (40 g of silica gel). It was eluted with dichloromethane containing 5% of methanol. The fractions containing the aimed product were collected, concentrate to dryness, suspended in 100 ml of a mixed solvent of ethyl acetate and hexane (1:1) and the resulting product was collected by filtration and washed with hexane to give 1.4 g of the title compound. The yield was 73%.

Workup

  1. customreacted at 100° C. in an autoclave for 8 hours
  2. concentrationconcentrated to dryness
  3. custompurified by a silica gel column (40 g of silica gel)
  4. washIt was eluted with dichloromethane containing 5% of methanol
  5. additionThe fractions containing the aimed product
  6. customwere collected
  7. concentrationconcentrate to dryness
  8. filtrationthe resulting product was collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-e23e6ad90bb1427cb78f131335699f34
Source dataset
uspto-grants-2006_05
Patent number
USRE039112E1

Reaction notes

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