Hydrochloric Acid → HCID 178478679, compound

HRID 887833Notes

Reaction equation

HRID 887833 reaction equation
[ClH:1].Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][N:12]2[CH2:16][C@H:15]3[C:17]4[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[CH:21][C:22]=4[O:23][CH2:24][C@@H:14]3[CH2:13]2)[CH2:6][CH2:5]1.[Cl:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[ClH:27].[ClH:1].[N:29]1[CH:30]=[CH:31][CH:32]=[N:33][C:28]=1[NH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][N:12]2[CH2:16][C@H:15]3[C:17]4[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[CH:21][C:22]=4[O:23][CH2:24][C@@H:14]3[CH2:13]2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 178478680HCID 178478680, compound

Product 1

HCID 178478679HCID 178478679, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 0.715 g of the compound of Example 1 (2.2 mmol), 0.303 mg of 2-chloropyrimidine and 0.47 g of sodium carbonate in 45 ml of ethanol is heated at reflux for 72 hours. After filtering, the solvents are then evaporated off After extraction with ethyl acetate and drying (MgSO4), evaporation yields an oil which is purified by chromatography on a silica column using a mixture of dichloromethane/methanol/ammonium hydroxide (98/2/0.2) as eluant to yield, after converting to a salt in ethanol in the warm state using 1N ethereal HCl, the title product.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 72 hours
  3. filtrationAfter filtering
  4. customthe solvents are then evaporated off
  5. extractionAfter extraction with ethyl acetate
  6. customdrying
  7. custom(MgSO4), evaporation
  8. customyields an oil which
  9. customis purified by chromatography on a silica column
  10. additiona mixture of dichloromethane/methanol/ammonium hydroxide (98/2/0.2) as eluant
  11. customto yield

Sources & evidence

ORD record
ord-b2e7b548bf164dc2901eb9fe4c40c5c7
Source dataset
uspto-grants-2012_08
Patent number
US08247441B2

Reaction notes

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