Diisopropylethylamine → HCID 71006785, compound

HRID 1505366Notes

Reaction equation

HRID 1505366 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:11]2[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].[CH3:18][C:19]([O:22][C:23]([NH:25][C@@H:26]([C:28](O)=[O:29])[CH3:27])=[O:24])([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(#N)C>[CH3:27][C@@H:26]([NH:25][C:23](=[O:24])[O:22][C:19]([CH3:21])([CH3:20])[CH3:18])[C:28]([NH:17][C:14]1[CH:13]=[N:12][C:11]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)=[N:16][CH:15]=1)=[O:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 61147393HCID 61147393, compound2×

Product 1

HCID 71006785HCID 71006785, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-{[3-(1-methylethyl)phenyl]oxy}-5-pyrimidinamine (Intermediate 85, 229 mg) in acetonitrile (20 mL) were added N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (378 mg, 2 mmol), HBTU (474 mg, 1.25 mmol) and DIPEA (387 mg, 3 mmol) and the mixture was heated at reflux and stirred overnight. The resulting mixture was concentrated under vacuum and water (100 mL) was added. It was extracted with ethyl acetate (3 times 100 mL) and the combined organic layers were dried over sodium sulphate and evaporated to afford a brown oil, which was purified by silica gel chromatography (mobile phase: ethyl acetate: petroleum ether=1/5−1/2) to afford the title compound (300 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. concentrationThe resulting mixture was concentrated under vacuum and water (100 mL)
  4. additionwas added
  5. extractionIt was extracted with ethyl acetate (3 times 100 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulphate
  7. customevaporated
  8. customto afford a brown oil, which
  9. customwas purified by silica gel chromatography (mobile phase: ethyl acetate: petroleum ether=1/5−1/2)

Sources & evidence

ORD record
ord-1d990d4233e942f7bf56b09f8db5d004
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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