Diisopropylethylamine → HCID 58125255, compound

HRID 646180

Reaction equation

HRID 646180 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17](O)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[CH3:45][O:46][C:47]([C:49]1[CH:54]=[CH:53][C:52]([C@@H:55]([NH3+:57])[CH3:56])=[CH:51][CH:50]=1)=[O:48].CCN(C(C)C)C(C)C>C(#N)C>[CH3:45][O:46][C:47]([C:49]1[CH:54]=[CH:53][C:52]([C@@H:55]([NH:57][C:17]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)=[O:18])[CH3:56])=[CH:51][CH:50]=1)=[O:48]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14977845N-Boc-indoline-7-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Product 1

HCID 58125255HCID 58125255, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (0.5 g, 1.9 mmol), HATU (795 mg, 2.09 mmol) and (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride (511 mg, 2.85 mmol) were added to acetonitrile (12.7 ml). The solution was cooled in an ice bath and DIPEA (993 ul, 5.7 mmol) was added. The ice bath was removed and the mixture stirred for 2 hours at RT. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 8.40 (d, 1H), 7.90 (d, 2H), 7.55 (d, 2H), 7.30 (d, 1H), 7.25 (d, 1H), 7.00 (t, 1H), 5.10 (m, 1H), 4.00 (m, 2H), 3.85 (s, 3H), 3.05 (m, 2H), 1.45 (d, 3H), 1.40 (s, 9H).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe ice bath was removed
  3. customThe solvent was removed
  4. customthe crude mixture purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-80c6e4df44d1416a96c6a608a50359a6
Source dataset
uspto-grants-2010_04
Patent number
US07705035B2

Linked notes

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