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4-Methylmorpholine → 2-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-[6-[5-[(ethenylsulfonyl)amino]-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 1695743
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695743
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([NH:25][C:26]([C:28]3[N:29]=[C:30]([CH2:33][N:34]4[CH2:39][C@H:38]([CH3:40])[O:37][C@H:36]([CH3:41])[CH2:35]4)[S:31][CH:32]=3)=[O:27])[C:13]3[C:17]([CH:18]=2)=[N:16][N:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:14]=3)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].CN1CCOCC1.Cl[CH2:50][CH2:51][S:52](Cl)(=[O:54])=[O:53]>C(Cl)Cl>[CH3:41][C@H:36]1[O:37][C@@H:38]([CH3:40])[CH2:39][N:34]([CH2:33][C:30]2[S:31][CH:32]=[C:28]([C:26]([NH:25][C:12]3[C:13]4[C:17]([CH:18]=[C:10]([C:4]5[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][S:52]([CH:51]=[CH2:50])(=[O:54])=[O:53])[CH:3]=5)[CH:11]=3)=[N:16][N:15]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[CH:14]=4)=[O:27])[N:29]=2)[CH2:35]1
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Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 58255790N-[6-[5-Amino-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide

Produkt 1

HCID 669112332-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-[6-[5-[(ethenylsulfonyl)amino]-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-[6-[5-Amino-6-(methyloxy)-3-pyridinyl]-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide (250 mg) was dissolved in DCM (6 ml) and N-methylmorpholine (0.143 ml) was added. The reaction was cooled to 0° C. in an ice bath, then 2-chloroethanesulfonyl chloride (0.047 ml) was added dropwise. The reaction was left to warm to RT overnight. Reaction had blown dry, so was redissolved in DCM (6 ml). Further 2-chloroethanesulfonyl chloride (0.047 ml) was added and stirred at RT for 2 hours. Water (6 ml) was added to the reaction. The DCM was separated, passed through a hydrophobic frit, then evaporated to dryness to give crude title compound (250 mg) used directly in the next step without further purification.

Aufarbeitung

  1. waitThe reaction was left
  2. temperatureto warm to RT overnight
  3. customReaction
  4. customhad blown dry
  5. dissolutionso was redissolved in DCM (6 ml)
  6. additionFurther 2-chloroethanesulfonyl chloride (0.047 ml) was added
  7. additionWater (6 ml) was added to the reaction
  8. customThe DCM was separated
  9. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3f2ecda3e6c54712b7e253593f95a53e
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163743B2

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