1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride → AT-Iap

HRID 1475529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475529
Cl.Cl.[F:3][C:4]1[CH:39]=[CH:38][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[N:17]([C:18](=[O:35])[CH2:19][N:20]4[CH2:25][C@@H:24]([CH3:26])[NH:23][CH2:22][C@@H:21]4[CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][C@H:29]4[CH3:34])[CH2:16][C:15]([CH3:37])([CH3:36])[C:12]3=[N:13][CH:14]=2)=[CH:6][CH:5]=1>O>[F:3][C:4]1[CH:39]=[CH:38][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[N:17]([C:18](=[O:35])[CH2:19][N:20]4[CH2:25][C@@H:24]([CH3:26])[NH:23][CH2:22][C@@H:21]4[CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][C@H:29]4[CH3:34])[CH2:16][C:15]([CH3:37])([CH3:36])[C:12]3=[N:13][CH:14]=2)=[CH:6][CH:5]=1

Komponenten

3

Edukt 1

HCID 714716131-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride

Produkt 1

HCID 70980530AT-IapAusbeute 109,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride (1.8 g) was dissolved in water (50 mL) and the resulting solution extracted with ethyl acetate (50 mL). The aqueous phase was basified (pH 8) with saturated aqueous NaHCO3 then was extracted with DCM (5×50 mL). The combined DCM extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound (1.72 g) as a foam. 1H NMR (Me-d3-OD): 8.24 (1H, s), 8.07 (1H, d), 7.24 (2H, dd), 7.03 (2H, t), 4.19-4.06 (1H, m), 3.99 (3H, d), 3.90 (1H, d), 3.71 (1H, d), 3.65-3.48 (2H, m), 3.19-2.70 (8H, m), 2.60-2.40 (2H, m), 2.26 (1H, s), 2.09-1.93 (1H, m), 1.87 (1H, d), 1.41 (6H, d), 1.04 (3H, d), 0.97 (3H, d).

Aufarbeitung

  1. extractionthe resulting solution extracted with ethyl acetate (50 mL)
  2. extractionthen was extracted with DCM (5×50 mL)
  3. dry with materialThe combined DCM extracts were dried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ac26ab26d0c442e7a458146e1686ff50
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018214B2

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