Diisopropylethylamine → HCID 69013806, compound

HRID 1371767Notes

Reaction equation

HRID 1371767 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-84151c360d744b4ebee4b462e0684f6c
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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