Hydrochloric Acid → HCID 66748186, compound

HRID 2401867Notes

Reaction equation

HRID 2401867 reaction equation
C(S([NH:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:9]1[C:13]([C:14]#[N:15])=[C:12]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:11][C:10]=1[C:22]([OH:24])=[O:23])=O)(C)(C)C.Cl>C(Cl)Cl>[ClH:31].[NH2:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:9]1[C:13]([C:14]#[N:15])=[C:12]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:11][C:10]=1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66748087HCID 66748087, compound

Product 1

HCID 66748186HCID 66748186, compoundYield 175.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{[(tert-butylsulfinyl)amino](4-chlorophenyl)methyl}-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylic acid (1.46 g, 3.03 mmol) in methylene chloride (25.0 mL) was slowly added hydrochloric acid (4M in 1,4-dioxane, 15.0 mL), and the resultant suspension was stirred at room temperature for 1 hour. The suspension was filtered through a fine frit funnel. The collected solid was washed with DCM and dried in vacuo to afford 3-[amino(4-chlorophenyl)methyl]-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylic acid hydrochloride (113) (1.10 g, yield 86.5%) as a white powder. LCMS: (FA) ES+ 378; ES− 376; 1H NMR (400 MHz, CD3OD) δ 7.44-7.90 (m, 4H), 5.84 (s, 1H), 3.81-3.84 (m, 4H), 3.64-3.67 (m, 4H).

Workup

  1. filtrationThe suspension was filtered through a fine frit funnel
  2. washThe collected solid was washed with DCM
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3d3c4cd5954746139da508dca12e0c5d
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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