Hydrochloric Acid → HCID 89781817, compound

HRID 2206329Notes

Reaction equation

HRID 2206329 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:20](=[O:21])[O:19][C:18]4[CH:17]=[C:16]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)[N:15]=[CH:14][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:20](=[O:21])[O:19][C:18]4[CH:17]=[C:16]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)[N:15]=[CH:14][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 71731023HCID 71731023, compound

Product 1

HCID 89781817HCID 89781817, compoundYield 147.5%

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[3,2-c]pyridin-7-yl)piperazine-1-carboxylate (96 mg, 0.19 mmol) in CH2Cl2 (2 mL) was added 4N HCl in dioxane (1 mL). The mixture was stirred for 6 hours, and filtered. The solid was washed with ether and dried under nitrogen to give 61 mg (82%) of 3-(4-chlorobenzo[d]thiazol-2-yl)-7-(piperazin-1-yl)-2H-pyrano[3,2-c]pyridin-2-one hydrochloride used in the next step without further purification. MS m/z 399.1 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.34 (2H, br), 9.13 (1H, s), 8.96 (1H, s), 8.16 (1H, d, J=6.94 Hz), 7.66 (1H, d, J=6.62 Hz), 7.46 (1H, t, J=7.88 Hz), 7.00 (1H, s), 4.01 (4H, m), 3.22 (4H, m).

Workup

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

Sources & evidence

ORD record
ord-4334f6649d0249a9a877aa547c670927
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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