Trifluoroacetic acid → HCID 178487965, compound

HRID 1422695Notes

Reaction equation

HRID 1422695 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[N:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29]C(=O)O)[CH2:25][CH2:24]1)=[CH:13]2>ClCCl>[CH3:8][O:9][C:10]1[N:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH2:21][CH2:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([NH2:29])[CH2:27][CH2:28]1)=[CH:13]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487967HCID 178487967, compound

Product 1

HCID 178487965HCID 178487965, compoundYield 95%

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 tort-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-d9215bfa12284db68a659efb91c882de
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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