Diisopropylethylamine → HCID 69013806, compound

HRID 1435347Notes

Reaction equation

HRID 1435347 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]1[OH:12].[NH2:13][C:14]1[C:19]([C:20]([C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([F:30])[C:23]=2[F:31])=[O:21])=[CH:18][N:17]=[C:16](Cl)[N:15]=1.C(N(C(C)C)CC)(C)C>C(O)C>[NH2:13][C:14]1[C:19]([C:20]([C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([F:30])[C:23]=2[F:31])=[O:21])=[CH:18][N:17]=[C:16]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]2[OH:12])[N:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21070550HCID 21070550, compoundHCID 21070647HCID 21070647, compound

Product 1

HCID 69013806HCID 69013806, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The amine (44 mg, 0.22 mmol, Example 305) and chloropyrimidine (55 mg, 0.18 mmol, Example 289) were dissolved in ethanol (5 mL). To the stirred mixture at reflux, diisopropylethylamine (64 uL, Aldrich) was added and the mixture was refluxed for 20 hours. The solvent was removed and the residue was purified by HPLC (10-60%, acetonitrile/water) to give a white solid, 25 mg, 30%. MS (ES) MH+=458.

Workup

  1. temperatureTo the stirred mixture at reflux
  2. temperaturethe mixture was refluxed for 20 hours
  3. customThe solvent was removed
  4. customthe residue was purified by HPLC (10-60%, acetonitrile/water)
  5. customto give a white solid, 25 mg, 30%

Sources & evidence

ORD record
ord-c796912d74da42b39ea89c85789b7654
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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