Sodium triacetoxyborohydride → (R)-N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)piperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

HRID 907314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907314
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[OH:32][CH2:33][C@H:34]1[CH2:39][NH:38][CH2:37][CH2:36][N:35]1C(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:27][CH2:28]3)[CH:18]=[C:17]4[CH2:29][N:38]3[CH2:37][CH2:36][NH:35][C@@H:34]([CH2:33][OH:32])[CH2:39]3)[CH:7]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Produkt 1

HCID 24994903(R)-N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)piperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 75 step i) (300 mg), (R)-2-(hydroxymethyl)piperazine-1-carboxylic acid, tert-butyl ester (465 mg) and sodium triacetoxyborohydride (608 mg) in dichloromethane (20 mL) was stirred under nitrogen for 16 hours. The reaction was partitioned between dichloromethane and water, the organics were then collected and concentrated to dryness. The residue was purified by HPLC to give the title compound (230 mg) as a solid.

Aufarbeitung

  1. customThe reaction was partitioned between dichloromethane and water
  2. customthe organics were then collected
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f5a001ebfc534820b1787e630f4b87ad
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012979B2

Notizen zur Reaktion

Wird geladen…