Hydrochloric Acid → HCID 178478678, compound

HRID 887832Notes

Reaction equation

HRID 887832 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.C(N(C(C)C)CC)(C)C.Cl.F[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1>C(O)C>[ClH:1].[ClH:1].[N:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=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 97462-FluoropyridineHCID 81531DiisopropylethylamineHCID 178478680HCID 178478680, compound

Product 1

HCID 178478678HCID 178478678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.482 g of the compound of Example 1 (1.48 mmol) and 0.245 ml of diisopropylethylamine in 5 ml of 2-fluoropyridine is heated at reflux for 24 hours. After evaporating off the solvents and then diluting with water, the mixture is extracted with ethyl acetate, dried (MgSO4) and evaporated. The residue obtained is purified by chromatography on a silica column using a mixture of dichloromethane/methanol/ammonium hydroxide (97/3/0.3) 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 24 hours
  3. customAfter evaporating off the solvents
  4. additiondiluting with water
  5. extractionthe mixture is extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a silica column
  10. additiona mixture of dichloromethane/methanol/ammonium hydroxide (97/3/0.3) as eluant
  11. customto yield

Sources & evidence

ORD record
ord-c850628b440e48e89c62e7028283b31e
Source dataset
uspto-grants-2012_08
Patent number
US08247441B2

Reaction notes

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