Trifluoroacetic acid → HCID 178487965, compound

HRID 2279294Notes

Reaction equation

HRID 2279294 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-d4d79f3af16c450fa8225e12e5e93d2c
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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