Hydrochloric Acid → HCID 59447037, compound

HRID 1946820Notes

Reaction equation

HRID 1946820 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:32][CH2:33][CH3:34])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:31]=[CH:30][C:18]([CH2:19][S:20]([CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])(=[O:22])=[O:21])=[CH:17][CH:16]=3)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.Cl>C1COCC1>[CH:1]1([CH2:4][N:5]([CH2:32][CH2:33][CH3:34])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:31]=[CH:30][C:18]([CH2:19][S:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:22])=[O:21])=[CH:17][CH:16]=3)=[O:13])[CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59446938HCID 59446938, compound

Product 1

HCID 59447037HCID 59447037, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-({4-[({6-[(cyclopropylmethyl)(propyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}sulfonyl)propanoate (Example 119, 120 mg, 0.25 mmol) in THF (5 ml) was treated with concentrated HCl (2 ml). After stirring at RT for 48 hours a further portion of concentrated HCl (5 ml) was added. After stirring for a further 72 hours, the solvent was reduced in vacuo to half the volume and the mixture extracted with EtOAc. The combined organic extracts were washed with water, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with DCM containing increasing amounts of methanol to give the title compound as a white solid (90 mg, 78%).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. washThe combined organic extracts were washed with water
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (silica)
  6. washeluting with DCM containing
  7. temperatureincreasing amounts of methanol

Sources & evidence

ORD record
ord-d0d1be3ddc194157b8fc49335bf5f05c
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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