Trifluoroacetic acid → HCID 178487965, compound

HRID 1019861Notes

Reaction equation

HRID 1019861 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][O:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[N:31][C:30]([O:34][CH3:35])=[CH:29][CH:28]=3)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[CH3:35][O:34][C:30]1[N:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][C@H:18]1[CH2:17][CH2:16][C@H:15]([NH2:14])[CH2:20][CH2:19]1)=[CH:33]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487968HCID 178487968, compound

Product 1

HCID 178487965HCID 178487965, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6.33 mL, 82.2 mmol, 20 eq) is added at room temperature to a stirred solution of {trans-4-[2-(6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.65 g, 4.11 mmol, 1.0 eq) in dichloromethane (100 mL). After 2 hours stirring at room temperature, the reaction mixture is partitioned between saturated sodium hydrogen carbonate aqueous solution and dichloromethane and the pH value is about 10. The combined organic layers are dried over sodium sulfate and concentrated to afford trans-4-[2-(6-methoxy-[1,5]naphthyridin-3-yloxy)-ethyl]-cyclohexylamine as a yellow solid (1.24 g, 95% yield).

Workup

  1. customthe reaction mixture is partitioned between saturated sodium hydrogen carbonate aqueous solution and dichloromethane
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c527e3fa967446a7a06fd5ba8fc6a3ef
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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