Hydrochloric Acid → HCID 178478769, compound

HRID 1186296Notes

Reaction equation

HRID 1186296 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[NH:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:25].CCOCC>CO>[ClH:25].[ClH:25].[N:1]1([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[NH:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178511961HCID 178511961, compound

Product 1

HCID 178478769HCID 178478769, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.16 g, 0.473 mmol) in methanol (3 mL) was treated with 1 N hydrochloric acid in ether (1.418 mL, 1.418 mmol) and stirred for 15 minutes at room temperature. Solvent was evaporated and product was dried under reduced pressure to obtain N-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-yl)thiophene-2-carboximidamide dihydrochloride (0.17 g, 0.413 mmol, 87% yield) as a solid. 1H NMR (DMSO-d6) δ 11.50 (s, 1H), 11.38 (s, 1H), 11.26 (brs, 1H), 9.71 (s, 1H), 8.64 (s, 1H), 8.20-8.17 (m, 2H), 7.75 (s, 1H), 7.53 (d, 1H, J=6.6 Hz), 7.39 (s, 2H), 7.12 (d, 1H, J=6.3 Hz), 3.58-3.52 (m, 2H), 3.40-3.32 (m, 2H), 3.20-3.16 (m, 2H), 3.06-3.04 (m, 2H), 2.00-1.88 (m, 4H); ESI-MS (m/z, %): 339 (MH+, free base, 100), 268 (74), 126 (59); ESI-HRMS calculated for C19H23N4S (MH+, free base), calculated: 339.1637; observed: 339.1649.

Workup

  1. customSolvent was evaporated
  2. customproduct was dried under reduced pressure

Sources & evidence

ORD record
ord-abe666bd44db4036ba163ba770290346
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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