Trifluoroacetic acid → HCID 24826059, compound

HRID 910928Notes

Reaction equation

HRID 910928 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>ClCCl>[OH:32][C:30]([C:29]([F:34])([F:33])[F:28])=[O:31].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24825875HCID 24825875, compound

Product 1

HCID 24826059HCID 24826059, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)piperidine-1-carboxylate (1.50 g, 3.84 mmol) in dichloromethane (10 mL) and added 2,2,2-trifluoroacetic acid (0.888 mL, 11.5 mmol). The reaction mixture was stirred at room temperature for 2 hours, then concentrated to provide 4-methyl-N-(4-(piperidin-4-yloxy)pyridin-2-yl)thiazol-2-amine TFA salt (1.6 g, 100%) as a light yellow solid. 1H NMR (DMSO) δ 8.53 (bs, 2H), 8.15 (d, 1H), 6.67 (dd, 1H), 6.61 (m, 1H), 6.56 (d, 1H), 4.74 (m, 1H), 3.25 (bm, 2H), 3.11 (bm, 2H), 2.23 (d, 3H), 2.10 (bm, 2H), 1.84 (bm, 2H); Mass spectrum (apci) m/z=291 (100) (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ccf339e6e68c43e1a347234e3af57735
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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