Trifluoroacetic acid → Morpholine-2-carboxylic acid [6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]amide

HRID 1401869Notes

Reaction equation

HRID 1401869 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][O:18][CH:17]([C:21](=[O:43])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[CH:38]=[CH:37][C:36]4[C:35]([CH3:40])([CH3:39])[CH2:34][CH2:33][C:32]([CH3:42])([CH3:41])[C:31]=4[CH:30]=3)[N:24]=2)[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:39][C:35]1([CH3:40])[CH2:34][CH2:33][C:32]([CH3:41])([CH3:42])[C:31]2[CH:30]=[C:29]([C:25]3[N:24]=[C:23]([NH:22][C:21]([CH:17]4[O:18][CH2:19][CH2:20][NH:15][CH2:16]4)=[O:43])[CH:28]=[CH:27][CH:26]=3)[CH:38]=[CH:37][C:36]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673232752-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 67249005Morpholine-2-carboxylic acid [6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The protecting group is cleaved off as already described using TFA in DCM starting from 92 mg (0.19 mmol) of 2-[6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester from step b. The product is purified by means of preparative HPLC and is in the form of the TFA salt.

Workup

  1. customThe product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-c9637eb2815a459eaea54e75fd37a05e
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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