Hydrochloric Acid → HCID 178478768, compound

HRID 1186293Notes

Reaction equation

HRID 1186293 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)=[NH:21])[CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1.[ClH:27]>CO>[ClH:27].[ClH:27].[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)=[NH:21])[CH:17]=3)[NH:12][CH:11]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178511960HCID 178511960, compound

Product 1

HCID 178478768HCID 178478768, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(3-(1-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.125 g, 0.341 mmol) in dry methanol (3 mL) was treated with hydrogen chloride (1M in diethyl ether) (1.023 mL, 1.023 mmol) at room temperature. Solvent was evaporated under reduced pressure after stirring for 15 minutes and the crude material was dried to obtain N-(3-(1-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide dihydrochloride (0.14 g, 93%) as a solid. 1H NMR (DMSO-d6) δ 11.70 (s, 1H), 11.47 (s, 1H), 10.57 (brs, 1H), 9.66 (s, 1H), 8.61 (s, 1H), 8.19-8.16 (m, 2H), 7.94 (s, 1H), 7.68 (d, 1H, J=2.1 Hz), 7.59 (d, 1H, J=8.4 Hz), 7.39 (t, 1H, J=4.5 Hz), 7.18 (d, 1H, J=9.3 Hz), 6.16 (s, 1H), 5.36 (s, 1H), 4.06-3.96 (m, 1H), 3.90-3.80 (m, 3H), 3.71-3.67 (m, 1H), 3.28-3.0 (m, 2H), 2.98-2.91 (m, 1H), 2.81-2.72 (m, 1H), 2.50-2.40 (m, 2H, merged with DMSO peak); ESI-MS (m/z, %): 367 (MH+, 39), 294 (100); ESI-HRMS calculated for C20H23N4OS (MH+, free base), calculated: 367.1587; observed: 367.1605.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. dry with materialthe crude material was dried

Sources & evidence

ORD record
ord-9e1c20a5eb3542c4b81a9c429a55fc0c
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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