Trifluoroacetic acid → Trifluoroacetic acid

HRID 1424635Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15]([NH:17][CH:18]3[CH:25]4[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)=[O:16])[CH2:11][CH2:10]1)[N:8](CC1C=CC(OC)=CC=1)[C:7]2([CH3:39])[CH3:38].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15]([NH:17][CH:18]3[CH:25]4[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:27][CH:19]3[CH2:20]5)[CH2:24]4)=[O:16])[CH2:11][CH2:10]1)[NH:8][C:7]2([CH3:39])[CH3:38].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58137297HCID 58137297, compound

Product 2

HCID 6422Trifluoroacetic acid

HCID 66953374HCID 66953374, compound

Conditions

Temperature: 80 °C

Procedure

Crude 7-chloro-N-(2-adamantyl)-2-(4-methoxybenzyl)-3,3-dimethylspiro[isoindoline-1,4′-piperidine]-1′-carboxamide was dissolved in neat TFA (3 mL) and the mixture was heated to 80° C. for 17 h. After this time LC-MS analysis showed complete removal of the p-methoxybenzyl group. The solution was evaporated the amine purified by prep HPLC to afford 7-chloro-N-(2-adamantyl)-3,3-dimethylspiro[isoindoline-1,4′-piperidine]-1′-carboxamide as its TFA salt. LC-MS Method 1 tR=1.43 min, m/z=428; 1H NMR (CD3OD) δ=7.47 (m, 2H), 7.37 (m, 1H), 4.22 (m, 2H), 3.89 (s, 1H), 3.21 (t, J=12.9, 2H).

Workup

customremoval of the p-methoxybenzyl group
customThe solution was evaporated the amine
custompurified by prep HPLC

Sources & evidence

ORD record: ord-e135ac62bf3d41d5959723be4e9bc79d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927715B2

Reaction notes

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