Hydrochloric Acid → Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-methyl-1H-indol-4-yl ester

HRID 48462Notes

Reaction equation

HRID 48462 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:21]N4CCOCC4)=[CH:15][N:16]3[CH2:19][CH3:20])=[C:12]([O:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH:11]=2)=[CH:4][N:3]=1.Cl>CO.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH3:21])=[CH:15][N:16]3[CH2:19][CH3:20])=[C:12]([O:28][S:29]([CH:32]([CH3:33])[CH3:34])(=[O:31])=[O:30])[CH:11]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86588575Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-4-yl ester

Product 1

HCID 86588574Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-methyl-1H-indol-4-yl esterYield 28.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-3-morpholin-4-ylmethyl-1H-indol-4-yl ester (Example 10d; 270 mg, 0.55 mmol) was dissolved in methanol (50 mL) and 1 M aqueous hydrochloric acid solution (0.6 mL) and hydrogenated at room temperature and atmospheric pressure for 16 h in the presence of palladium on activated charcoal (10%, 170 mg). The catalyst was removed by filtration through filter aid and the filtrate was concentrated. The residue was dissolved in water (10 mL) and the pH set to ≈9 with 25% aqueous ammonia solution. The precipitate was collected by filtration and purified by preparative HPLC to afford the title compound (63 mg, 28%). Off-white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. filtrationthrough filter aid
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in water (10 mL)
  5. filtrationThe precipitate was collected by filtration
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-30e2de28c785469084b6ac0c29bbbeec
Source dataset
uspto-grants-2004_03
Patent number
US06703397B2

Reaction notes

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