Trifluoroacetic acid → 2-(3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetic acid trifluoroacetate salt

HRID 1426110Notes

Reaction equation

HRID 1426110 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[C:18]([NH:23][C:24]3[S:25][CH:26]=[C:27]([CH3:29])[N:28]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:10]=1)(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>C(Cl)Cl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH3:29][C:27]1[N:28]=[C:24]([NH:23][C:18]2[C:17]([O:16][CH2:15][C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[O:8][CH2:7][C:6]([OH:30])=[O:5])=[CH:22][CH:21]=[CH:20][N:19]=2)[S:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59225697Tert-butyl 2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetate

Product 1

HCID 166603332-(3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetic acid trifluoroacetate saltYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetate (680 mg, 1.59 mmol) and CH2Cl2 (5 mL) were combined in a 50 mL round-bottomed flask. Trifluoroacetic acid (5 mL) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and the resultant solid was triturated with 40% methanol in CH2Cl2 to provide 2-(3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenoxy)acetic acid trifluoroacetate salt (621 mg, 80.4% yield) as a white solid. 1H NMR (d6-DMSO) δ 7.92 (dd, 1H), 7.49 (dd, 1 h), 7.32 (t, 1H), 7.16 (m, 2H), 7.00 (dd, 1 h), 6.88 (dd, 1H), 6.72 (q, 1H), 5.26 (s, 2H), 4.69 (s, 2h), 2.29 (d, 3H). Mass spectrum (apci) m/z=372 (M+H-TFA).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resultant solid was triturated with 40% methanol in CH2Cl2

Sources & evidence

ORD record
ord-8d6b76dd49134dddb76b94a624667f77
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…