Diisopropylethylamine → tert-Butyl (4aR,7aS)-2-benzamido-7a-[3-[(5-fluoropyridine-2-carbonyl)amino]phenyl]-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

HRID 77578

Reaktionsgleichung

Reaktionsgleichung von HRID 77578
[NH2:1][C:2]1[CH:3]=[C:4]([C@:8]23[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][C@H:13]2[CH2:12][S:11][C:10]([NH:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:9]3)[CH:5]=[CH:6][CH:7]=1.[F:33][C:34]1[CH:35]=[CH:36][C:37]([C:40](O)=[O:41])=[N:38][CH:39]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)C(C)CN=C=NCC.C(N(C(C)C)CC)(C)C>ClCCl.C(=O)(O)[O-].[Na+].CN(C)C=O>[C:25]([NH:24][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@:8]2([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:40]([C:37]3[CH:36]=[CH:35][C:34]([F:33])=[CH:39][N:38]=3)=[O:41])[CH:3]=2)[N:9]=1)(=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

9

Edukt 5

HCID 81531DiisopropylethylamineHCID 27628765-fluoropyridine-2-carboxylic AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 219312251-(2-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 86762764tert-butyl (4aR,7aS)-7a-(3-aminophenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Produkt 1

HCID 86762763tert-Butyl (4aR,7aS)-2-benzamido-7a-[3-[(5-fluoropyridine-2-carbonyl)amino]phenyl]-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A slurry of tert-butyl (4aR,7aS)-7a-(3-aminophenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (93 mg, 0.21 mmol), 5-fluoropyridine-2-carboxylic acid (31.9 mg, 0.23 mmol), 1-hydroxybenzotriazole hydrate (56.7 mg, 0.41 mmol) and 1-(2-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40 mg, 0.21 mmol) in dichloromethane (4 mL) containing dimethylformamide (1 ml) is treated with diisopropylethylamine (179.2 μL, 1.03 mmol) and the resulting mixture is stirred at room temperature overnight. The reaction mixture is diluted with dichloromethane (5 mL) and saturated aqueous sodium bicarbonate (15 mL). The organic layer is separated and washed with saturated aqueous sodium chloride (10 mL), dried over sodium sulfate, filtered, and the solvent removed in vacuo to give the crude title compound (105 mg, 89%). ES/MS (m/e): 576 (M+H).

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with saturated aqueous sodium chloride (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fab49d5fda4d43b78d03e8e0c3bda205
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841293B1

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