Triethylamine → HCID 9908680, compound

HRID 2114961Notes

Reaction equation

HRID 2114961 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:17])[C:14]([OH:16])=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[CH2:31]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:17])[C:14]([NH:27][C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[NH:33][C:32](=[O:37])[CH2:31]4)=[O:16])[CH2:11][CH2:12]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27732135-Amino-2-oxindoleHCID 51342220[4-(4-Fluorobenzyl)piperidin-1-yl](oxo)acetic acid

Product 1

HCID 9908680HCID 9908680, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.2 g (12 mmol) of [4-(4-fluoro-benzyl)-piperidin-1-yl]-oxo-acetic acid, 1.4 ml (10 mmol) of triethylamine, 1.5 g (10 mmol) of 5-amino-1,3-dihydro-indol-2-one [Tetrahedron, 24, 1376. (1957)] 3.8 g (10 mmol) of HBTU [O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (Advanced Chem. Tech.)] and 100 ml of dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is concentrated. Then 150 ml of 8% sodium hydrogencarbonate solution and 150 ml of chloroform is added to the mixture. The organic layer is separated and the water phase is extracted three times with 25 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and chloroform:methanol=19:1 as eluent to yield 2.67 g (68%) of the title compound. Melting Point: 195-197° C. (diethylether)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionThen 150 ml of 8% sodium hydrogencarbonate solution and 150 ml of chloroform is added to the mixture
  3. customThe organic layer is separated
  4. extractionthe water phase is extracted three times with 25 ml of chloroform
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-e031b38b22c84f8196599bfdcf1d8bbd
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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