Hydrochloric Acid → HCID 178520128, compound

HRID 1845774Notes

Reaction equation

HRID 1845774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[CH2:18][O:19][Si](C(C)C)(C(C)C)C(C)C)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].Cl>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[CH2:18][OH:19])=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178460981HCID 178460981, compound

Product 1

HCID 178520128HCID 178520128, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carboximidamide (10.0 mg, 0.0218 mmol) was stirred in MeOH (500 μL) and hydrogen chloride in 1,4-dioxane (500 μL, 4.0 M) was added. The mixture was stirred for 30 min at rt. Purification by preparative LCMS gave the desired product (2.8 mg, 42%). 1H NMR (400 MHz, d6-DMSO): δ□ 11.00 (s, 1H), 8.99 (s, 1H), 7.09 (m, 1H), 6.82 (m, 1H), 6.53 (m, 1H), 5.92 (s, 1H), 4.95 (s, 1H). MF=C10H8ClFN4O2S; LCMS calculated for C10H9ClFN4O2S (M+H)+: m/z=303.0.

Workup

  1. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-55fb92aeaf074f7b8bfce2bcb3dc876b
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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