Hydrochloric Acid → HCID 25020401, Verbindung

HRID 907337

Reaktionsgleichung

Reaktionsgleichung von HRID 907337
[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[NH:39][CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+].Cl>ClCCl.C(O)(=O)C.O1CCOCC1.CO>[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:39]3[CH2:38][CH2:37][NH:36][CH2:35][C@H:34]3[CH2:33][OH:32])[CH:7]=2)[CH2:2][CH2:3]1

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Produkt 1

HCID 25020401HCID 25020401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The product of Example 75 step i) (0.4 g), (S)-3-hydroxymethyl-piperazine-1-carboxylic acid, tert-butyl ester (0.83 g) and sodium triacetoxyborohydride (0.81 g) were stirred in dichloromethane (20 mL) at room temperature for 12 hours. A few drops of acetic acid were added and stirring continued for 12 hours. Methanol (10 ml) and sodium cyanoborohydride (0.70 g) were added and stirring continued for a further 12 hours. Methanol (10 ml) and 4M HCl in 1,4-dioxane (10 ml) were added and stirred for 12 hours. The volatiles were removed under vacuum, dilute aqueous ammonia was added and the mixture extracted into dichloromethane. The organics were combined and evaporated under reduced pressure. The residue was purified by HPLC to give the title compound (0.035 g) as a solid.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for a further 12 hours
  3. stirringstirred for 12 hours
  4. customThe volatiles were removed under vacuum, dilute aqueous ammonia
  5. additionwas added
  6. extractionthe mixture extracted into dichloromethane
  7. customevaporated under reduced pressure
  8. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e0d336717db14615b82301be90259508
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012979B2

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