Diisopropylethylamine → tert-Butyl (1R,2S)-2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 516061

Reaktionsgleichung

Reaktionsgleichung von HRID 516061
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])[CH2:10][C:6]=2[C:5]([F:23])=[C:4](Cl)[N:3]=1.[NH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].CCN(C(C)C)C(C)C>C(#N)C.CO>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])[CH2:10][C:6]=2[C:5]([F:23])=[C:4]([NH:25][C@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]2[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[N:3]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamineHCID 583175754,6-dichloro-2-[(2,4-dimethoxyphenyl)methyl]-7-fluoro-1H,2H,3H-pyrrolo[3,4-c]pyridin-3-one

Produkt 1

HCID 86654721tert-Butyl (1R,2S)-2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamateAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (316 mg, 0.851 mmol) and cis-tert-butyl 2-aminocyclohexylcarbamate (365 mg, 1.703 mmol) and DIPEA (0.743 mL, 4.26 mmol) in ACN (2 mL) was stirred at 85° C. for 3 d. The resulting crude material was reconstituted in MeOH (1 mL) and purified by preparative HPLC. The fractions were collected and stripped to dryness via rotary evaporation to yield the title compound (161 mg, 34%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.35 (br s, 10 H), 1.58 (br s, 2 H), 1.76 (br s, 2 H), 3.71-3.90 (m, 11 H), 4.33 (br s, 2 H), 4.51 (br s, 2 H), 6.43-6.72 (m, 3 H), 6.87 (br s, 1 H), 7.07 (br s, 1 H). [M+H] calc'd for C27H34ClFN4O5, 549; found, 549.

Aufarbeitung

  1. custompurified by preparative HPLC
  2. customThe fractions were collected
  3. customstripped to dryness via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-bb4374755f8b4ce6b5d69de28b228338
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

Verknüpfte Notizen

Wird geladen…