Methanol → (2R)-2-amino-5-({2-[(carboxymethyl)amino]-1-[({3-{[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]amino}-1-[(dimethylamino)methyl]-3-oxopropyl}sulfanyl)methyl]-2-oxoethyl}amino)-5-oxopentanoic acid

HRID 2416086

Reaktionsgleichung

Reaktionsgleichung von HRID 2416086
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:29][CH2:30][CH3:31])=[C:17]([NH:20][C:21](=[O:28])[CH:22]=[CH:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:32]#[N:33])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:34][C@@H:35]([CH2:39][CH2:40][C:41]([NH:43][C@H:44]([C:47]([NH:49][CH2:50][C:51]([OH:53])=[O:52])=[O:48])[CH2:45][SH:46])=[O:42])[C:36]([OH:38])=[O:37].C(N(CC)CC)C.CO>O1CCCC1.O>[NH2:34][C@H:35]([CH2:39][CH2:40][C:41]([NH:43][CH:44]([CH2:45][S:46][CH:23]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:22][C:21]([NH:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:29][CH2:30][CH3:31])[N:13]=[CH:12][C:11]([C:32]#[N:33])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)=[O:28])[C:47]([NH:49][CH2:50][C:51]([OH:53])=[O:52])=[O:48])=[O:42])[C:36]([OH:38])=[O:37]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 124886GlutathioneHCID 216467N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide

Produkt 1

HCID 69462181(2R)-2-amino-5-({2-[(carboxymethyl)amino]-1-[({3-{[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]amino}-1-[(dimethylamino)methyl]-3-oxopropyl}sulfanyl)methyl]-2-oxoethyl}amino)-5-oxopentanoic acidAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.50 g (1.07 mmol) of 4-dimethylamino-but-2-enoic acid [4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-ethoxy-quinolin-6-yl]-amide, 0.328 g (1.07 mmol) of glutathione, and 0.2 mL of triethylamine in a solvent mixture consisting of 10 mL of methanol, 4 mL of water, and 4 mL of tetrahydrofuran was stirred for 7 h and then stored overnight in the refrigerator. The solvents were remove at reduced pressure at 30° C. Ethanol was added and removed three times giving 0.81 g of the title compound as a tan powder. A sample of this was purified by HPLC. The product was then isolated as the trifluoroacetate salt. Analysis for C34H40N8O8CIFS+(C2HF3O2)3; calcd: C, 43.00, H, 3.88, N, 10.03, Cl, 3.17; found: C, 42.23, H, 4.17, N, 10.03, Cl, 3.23.

Aufarbeitung

  1. waitstored overnight in the refrigerator
  2. customThe solvents were remove at reduced pressure at 30° C
  3. additionEthanol was added
  4. customremoved three times

Quellen und Nachweise

ORD-Eintrag
ord-98e997fe2d7242d6989f8e91b489a23b
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821988B2

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