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Triethylamine → tert-Butyl 16-oxo-15-{3-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]prop-2-yn-1-yl}-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

HRID 1615853
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1615853
[O:1]=[C:2]1[C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][C:4]2([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]1[CH2:25][C:26]#[CH:27].I[C:29]1[CH:30]=[C:31]2[C:44](=[CH:45][CH:46]=1)[CH2:43][C@:33]1([C:41]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]1=[O:42])[CH2:32]2.C(N(CC)CC)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[O:1]=[C:2]1[C:7]2([CH2:8][CH2:9][CH2:10][CH2:11]2)[N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][C:4]2([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:3]1[CH2:25][C:26]#[C:27][C:29]1[CH:30]=[C:31]2[C:44](=[CH:45][CH:46]=1)[CH2:43][C@:33]1([C:41]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]1=[O:42])[CH2:32]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 58118662(2R)-5-iodo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×HCID 58118691tert-Butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate2×

Produkt 1

HCID 66864621tert-Butyl 16-oxo-15-{3-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]prop-2-yn-1-yl}-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred suspension of tert-butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate (110 mg, 0.294 mmol, described in Intermediate 23), (2R)-5-iodo-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (106 mg, 0.294 mmol, described in Intermediate 27), tetrakis(triphenylphosphine)palladium(0) (34 mg, 0.029 mmol), copper(I)iodide (23 mg, 0.121 mmol), and triethylamine (0.082 mL, 0.588 mmol) in degassed DMF (1.5 mL) was heated at 50° C. for 30 min. The reaction was quenched with water (30 mL), partitioned with saturated NaHCO3 solution (30 mL) and extracted with EtOAc (2×60 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to yield the title compound. MS: m/z=609 (M+1).

Aufarbeitung

  1. customThe reaction was quenched with water (30 mL)
  2. custompartitioned with saturated NaHCO3 solution (30 mL)
  3. extractionextracted with EtOAc (2×60 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified on silica gel
  8. washeluting with a gradient of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-49f50a7915e04da5b33884f9b81d94bb
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765759B2

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