Hydrochloric Acid → HCID 178507244, compound

HRID 1453619Notes

Reaction equation

HRID 1453619 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:19]=[C:18]([NH:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([NH:27]C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[N:17]=[C:16]3[C:12]=1[N:13]=[CH:14][N:15]3C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.Cl.CO.ClCCl>CO.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:19]=[C:18]([NH:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]3)[N:17]=[C:16]3[C:12]=1[N:13]=[CH:14][NH:15]3)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21226129Dichloromethane methanolHCID 178454025HCID 178454025, compound

Product 1

HCID 178507244HCID 178507244, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

200 mg of product obtained in stage 4 of example 41 are dissolved in 5 ml of methanol. 5 ml of a 2N solution of hydrochloric acid in methanol are added. Stirring is carried out for 48 hours at ambient temperature, followed by evaporation to dryness. The residue is chromatographed on a silica column, eluting with 85/15/1.5 dichloromethane/methanol/aqueous ammonia. The product obtained is taken up in 10 ml of a 50/50 methanol/dichloromethane mixture, 6 ml of 1M HCl solution in ethyl acetate are added, the mixture is left to crystallize, filtration is carried out, and 87 mg of expected product are thus recovered.

Workup

  1. customfollowed by evaporation to dryness
  2. customThe residue is chromatographed on a silica column
  3. washeluting with 85/15/1.5 dichloromethane/methanol/aqueous ammonia
  4. customThe product obtained
  5. additionare added
  6. waitthe mixture is left
  7. customto crystallize
  8. filtrationfiltration
  9. custom87 mg of expected product are thus recovered

Sources & evidence

ORD record
ord-7117efb0d0b74a188e2ceec005292a4f
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Reaction notes

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