Hydrochloric Acid → HCID 89781818, compound

HRID 2206323Notes

Reaction equation

HRID 2206323 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:33](=[O:34])[O:32][C:14]4=[N:15][C:16]([N:19]5[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]5)=[CH:17][CH:18]=[C:13]4[CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl>C(Cl)Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:33](=[O:34])[O:32][C:14]4=[N:15][C:16]([N:19]5[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]5)=[CH:17][CH:18]=[C:13]4[CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89793953HCID 89793953, compound

Product 1

HCID 89781818HCID 89781818, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of t-butyl 4-(3-(4-chlorobenzo[d]thiazol-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)piperazine-1-carboxylate (850 mg, 1.7 mmol) in CH2Cl2 (15 mL) was added 4N HCl in dioxane (5 mL). The mixture was stirred for 16 hours, and filtered. The solid was washed with ether and dried under nitrogen. 3-(4-Chlorobenzo[d]thiazol-2-yl)-7-(piperazin-1-yl)-2H-pyrano[2,3-b]pyridin-2-one hydrochloride was obtained quantitatively and used for the next step without further purification. MS m/z 399.1 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.12 (1H, s), 9.11 (2H, br), 8.36 (1H, d, J=8.8 Hz), 8.16, (1H, d, J=6.9 Hz), 7.66 (1H, d, J=8.8 Hz), 7.45 (1H, t, J=7.9 Hz), 7.14 (1H, d, J=8.8 Hz), 4.03 (4H, m), 3.26 (4H, m).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with ether
  3. customdried under nitrogen

Sources & evidence

ORD record
ord-951312709554438da1aeb99cdf81f9ee
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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