Hydrochloric Acid → HCID 178482139, compound

HRID 1186277Notes

Reaction equation

HRID 1186277 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])[CH:16]=3)[NH:11][CH:10]=2)[CH2:4]1.[ClH:26]>CO>[ClH:26].[ClH:26].[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])[CH:16]=3)[NH:11][CH:10]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178482138HCID 178482138, compound

Product 1

HCID 178482139HCID 178482139, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(3-(3-(Methylamino)cyclohexyl)-1H-indol-5-yl)thiophene-2-carboximidamide [(+)-cis-enantiomer] (0.16 g, 0.45 mmol) was dissolved in a minimum amount of methanol to which hydrochloric acid (1.00 mL, 1.00 mmol, 1M in diethyl ether) was added. The mixture was left to stir for 1 hour at room temperature. The solvent was evaporated and the resulting solid dried under vacuum to give the product (0.16 g, 97%) as a light yellow solid. 1H-NMR (MeOH-d4) δ 1.30-1.67 (m, 4H), 1.93-2.24 (m, 3H), 2.47-2.51 (m, 1H), 2.73 (s, 3H), 2.96-309 (m, 1H), 7.16 (d, 1H, J=8.7 Hz), 7.25 (s, 1H), 7.38 (dd, 1H, J=4.5, 8.4 Hz), 7.56 (d, 1H, J=8.4 Hz), 7.73 (s, 1H), 8.05-8.07 (m, 2H); ESI-MS (m/z, %) 322 (100), 353 (MH+, free base, 50), ESI-HRMS calc. for C16H25N4O5 (MH+, free base), calculated: 353.1819. found: 353.1807.

Workup

  1. additionwas added
  2. waitThe mixture was left
  3. customThe solvent was evaporated
  4. customthe resulting solid dried under vacuum

Sources & evidence

ORD record
ord-8e3b417ed6874889b18712a421361eb1
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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