HCID 131734019, compound → Trifluoroacetic acid

HRID 713260Notes

Reaction equation

HRID 713260 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].C([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[N:18][C:19]([N:30]3[CH2:35][CH2:34][CH:33]([O:36][C:37]4[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=4[F:45])[CH2:32][CH2:31]3)=[C:20]([NH:25][CH:26]3[CH2:29][CH2:28][CH2:27]3)[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[CH:26]1([NH:25][C:20]2[N:21]=[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]3=[N:18][C:19]=2[N:30]2[CH2:31][CH2:32][CH:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=3[F:45])[CH2:34][CH2:35]2)[CH2:29][CH2:28][CH2:27]1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

5

Reactant 1

HCID 131734019HCID 131734019, compound

Product 2

HCID 6422Trifluoroacetic acidYield 474.2%HCID 118159348HCID 118159348, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-benzyl-N-cyclobutyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (85.2 mg, 0.135 mmol) and Pd(OH)2 on carbon (10 mg, 0.071 mmol) in THF (674 μL) was stirred at rt under an atmosphere of hydrogen gas (balloon). After 4 h, the mixture was filtered, washing with MeOH, and concentrated to afford the title compound as its TFA salt (73 mg, 100%) as a yellow solid, which was used without further purification. ESI-MS m/z [M+H]+ 428.4.

Workup

  1. filtrationthe mixture was filtered
  2. washwashing with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c848c6ebfba4f22b42610ea3cdc03cb
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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