Triethylamine → HCID 178491846, compound

HRID 1371753Notes

Reaction equation

HRID 1371753 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]2)[N:3]=1.C(N(CC)CC)C.Br[CH2:36][CH2:37][OH:38]>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][CH2:36][CH2:37][OH:38])[CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 178491845HCID 178491845, compound

Product 1

HCID 178491846HCID 178491846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trans-[4-amino-2-(4-amino-cyclohexylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (100 mg, 0.27 mmol, Example 120) and triethylamine (200 uL) in tetrahydrofuran (3 mL), 2-bromoethanol (20 uL, 0.28 mmol, Aldrich) was added and the mixture was stirred at reflux for 5 hours. The reaction was quenched with water and the mixture was extracted with ethyl acetate (3×10 mL) and the extracts were dried with sodium sulfate. Removal of solvent gave a yellow solid which was purified by reverse phase HPLC to give a pale yellow solid. 86 mg, 75%. MS (ES) MH+=422. CDK4 IC50=0.020 μM; CDK1 IC50=0.018 μM; CDK2 IC50=0.005 μM; HCT 116 IC90=0.179 μM.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  4. dry with materialthe extracts were dried with sodium sulfate
  5. customRemoval of solvent
  6. customgave a yellow solid which
  7. customwas purified by reverse phase HPLC
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-76f15950a08f4d16b79ee19a4c0c4123
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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