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Diisopropylethylamine → Methyl 4-(1-(indoline-7-carboxamido)cyclopropyl)benzoate

HRID 1694376
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1694376
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([OH:19])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:44][C:45]1([C:48]2[CH:57]=[CH:56][C:51]([C:52]([O:54][CH3:55])=[O:53])=[CH:50][CH:49]=2)[CH2:47][CH2:46]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(#N)C>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([NH:44][C:45]2([C:48]3[CH:57]=[CH:56][C:51]([C:52]([O:54][CH3:55])=[O:53])=[CH:50][CH:49]=3)[CH2:47][CH2:46]2)=[O:19])[CH2:10][CH2:9]1
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Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 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 45140209Methyl 4-(1-aminocyclopropyl)benzoate

Produkt 1

HCID 58017568
Methyl 4-(1-(indoline-7-carboxamido)cyclopropyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (300 mg, 1.14 mmol), HATU (475 mg, 21.2 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (262 mg, 1.37 mmol) were added to acetonitrile (7.6 ml). The solution was cooled in an ice bath and DIPEA (695 ul, 3.99 mmol) was added. After 2 hr at RT, the mixture was poured into a solution of NaHCO3 (½ sat.) and washed 3 times with EtOAc. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. The Boc group was removed with 1:1 TFA/DCM using the standard procedure.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. washwashed 3 times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed
  6. customthe crude mixture purified by flash chromatography on silica gel
  7. customThe Boc group was removed with 1:1 TFA/DCM using the standard procedure

Quellen und Nachweise

ORD-Eintrag
ord-6ccbfe3566654562ad5557ca8317821b
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08158671B2

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