Diisopropylethylamine → HCID 67010368, compound

HRID 1630066Notes

Reaction equation

HRID 1630066 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH3:21])[CH2:10][C@H:9]1[C:22](O)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:39]=[CH:38][C:29]([O:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@H:11]2[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:22](=[O:23])[NH:35][C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]4[CH:38]=[CH:39][C:26]([F:25])=[CH:27][CH:28]=4)=[CH:37][CH:36]=3)[CH2:10]2)=[C:15]([CH3:21])[CH:16]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58522988HCID 58522988, compound

Product 1

HCID 67010368HCID 67010368, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluoro-2-methylbenzyl)pyrrolidine-2-carboxylic acid (540 mg, 1.54 mmol), prepared as in Reference 4, 4-(4-fluorophenoxy)aniline (313 mg, 1.54 mmol), DIEA (0.4 mL) and HATU (586 mg, 1.54 mmol) in DMF (3 mL) was stirred at ambient temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate (20 mL) and then brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Product was purified from the residue by flash column (eluted with a 3:1 hexanes/ethyl acetate mixture) to give (2S,4R)-tert-butyl 4-(4-fluoro-2-methylbenzyl)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate (826 mg, 1.59 mmol, 103%) as a reddish oil.

Workup

  1. washwashed with saturated sodium bicarbonate (20 mL)
  2. dry with materialbrine (20 mL), dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customProduct was purified from the residue by flash column (
  5. washeluted with a 3:1 hexanes/ethyl acetate mixture)

Sources & evidence

ORD record
ord-32d1080f1a6f4850a0f7dd509367a642
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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