Diisopropylethylamine → HCID 86727255, compound

HRID 2173058Notes

Reaction equation

HRID 2173058 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[O:21][CH3:22])[CH:10]([CH3:11])[C:6]=2[C:5]([F:24])=[C:4](Cl)[N:3]=1.[NH2:26][C@@H:27]1[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]1[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[O:21][CH3:22])[CH:10]([CH3:11])[C:6]=2[C:5]([F:24])=[C:4]([NH:26][C@@H:27]2[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[N:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 68077633tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamateHCID 86727251HCID 86727251, compound

Product 1

HCID 86727255HCID 86727255, compoundYield 16%

Conditions

Temperature
95 °C

Procedure

To a sealed tube was added 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1-methyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (430 mg, 1.12 mol), tert-butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate (7.5 g, 34.2 mol), and DIPEA (0.97 mL, 5.58 mmol). The mixture was heated in the sealed tube at 95° C. for 72 h. The mixture was purified via preparative HPLC to give the title compound as a yellow solid (100 mg, 16%). [M+H] calc'd for C27H34ClFN4O6, 565. found, 565.

Workup

  1. customThe mixture was purified via preparative HPLC

Sources & evidence

ORD record
ord-523083888a1d49bda90bd411bb76076a
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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