Hydrochloric Acid → HCID 66995297, compound

HRID 911913Notes

Reaction equation

HRID 911913 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:7]=[C:8]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[N:14]=2)=[N:10][CH:11]=1.[ClH:35].CCOCC>C(Cl)Cl>[ClH:35].[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:7]=[C:8]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[N:14]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57742918HCID 57742918, compound

Product 1

HCID 66995297HCID 66995297, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10 mL round-bottom flask was charged with 5-(3-bromophenoxy)-3-(3-methoxyphenylthio)-N-(3-(tetrahydrofuran-2-yl)-1,2,4-thiadiazol-5-yl)pyridin-2-amine (20 mg, 0.036 mmol) and dissolved in CH2Cl2 (1 mL). 2M HCl in ether (0.1 mL, 0.2 mmol) was added and the solvent removed to afford the title compound (21 mg, 100%). 1H NMR (d6-DMSO) δ 11.51 (bs, 1H), 8.40 (d, 1H), 8.36 (bs, 1H), 7.68 (bs, 1H), 7.51-7.18 (m, 5H), 7.10-6.73 (m, 3H), 4.10-3.74 (m, 3H), 3.72 (s, 3H), 2.25 (m, 4H). Mass spectrum (apci) m/z=559.1 (M+H−HCl).

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-4eac3f9073684ab29365e3c088b4a0ce
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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