Hydrochloric Acid → HCID 24826503, compound

HRID 910970Notes

Reaction equation

HRID 910970 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=3)[O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.FC(F)(F)C(O)=O.[ClH:37]>ClCCl.CCOCC>[ClH:37].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=3)[O:18][CH2:19][C:20]([OH:22])=[O:21])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acid2×HCID 24826502HCID 24826502, compound

Product 1

HCID 24826503HCID 24826503, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenoxy)acetate (0.530 g, 1.28 mmol) was dissolved in dichloromethane (5 mL), and trifluoroacetic acid (5 mL) was added. The reaction mixture was stirred at room temperature for one hour, the concentrated. The TFA salt was dissolved in ether (15 mL). 1M HCl in ether (6 mL) was added, and the solids were collected by filtration, washed with hexanes and dried to afford the desired product as a white solid. 1H NMR (d6-DMSO) δ 11.85 (bs, 1H), 8.25 (d, 1H), 7.41 (t, 1H), 6.88 (d, 1H), 6.80-6.83 (m, 2H), 6.67-6.70 (m, 2H), 4.72 (s, 2H), 2.26 (s, 3H).

Workup

  1. filtrationthe solids were collected by filtration
  2. washwashed with hexanes
  3. customdried

Sources & evidence

ORD record
ord-a0e3f0430f444582b787670cc4bac68a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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