Diisopropylethylamine → HCID 86654743, compound

HRID 2092878Notes

Reaction equation

HRID 2092878 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[O:22][CH3:23])[C:10]([CH3:12])([CH3:11])[C:6]=2[C:5]([F:25])=[C:4](Cl)[N:3]=1.[NH2:27][C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@@H:29]1[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38].C(N(C(C)C)C(C)C)C>C(#N)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[O:22][CH3:23])[C:10]([CH3:12])([CH3:11])[C:6]=2[C:5]([F:25])=[C:4]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@@H:29]2[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 86654744HCID 86654744, compound

Product 1

HCID 86654743HCID 86654743, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

In a 10 mL sealed cap glass vial, 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1,1-dimethyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (50 mg, 0.125 mmol) and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (53.2 mg, 0.250 mmol) were dissolved in ACN (2 mL). N-ethyldiisopropylamine (0.033 mL, 0.188 mmol) was added, the cap was sealed, and the reaction mixture heated at 95° C. for 72 h. The reaction mixture was subsequently purified by preparative HPLC and basified to give the title compound as a light yellow solid (40 mg, 55%). [M+H] calc'd for C29H38ClFN4O5, 578.1. found, 577.4.

Workup

  1. customIn a 10 mL sealed
  2. customthe cap was sealed
  3. customThe reaction mixture was subsequently purified by preparative HPLC

Sources & evidence

ORD record
ord-14dd0eecb4314d67a73d1d8fd131db13
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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