Guanidine Hydrochloride → HCID 66748182, compound

HRID 2402085Notes

Reaction equation

HRID 2402085 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[S:10][C:11]=2[C:12](=O)/[CH:13]=[CH:14]/N(C)C)=[CH:4][CH:3]=1.Cl.[NH2:28][C:29]([NH2:31])=[NH:30].[O-]CC.[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)[S:10][C:11]=2[C:12]2[CH:13]=[CH:14][N:28]=[C:29]([NH2:31])[N:30]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2723922Sodium ethoxideHCID 66749245HCID 66749245, compound

Product 1

HCID 66748182HCID 66748182, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-1-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-3-(dimethylamino)prop-2-en-1-one (93.0 mg, 0.242 mmol) in isopropyl alcohol (1.0 mL) was added guanidine hydrochloride (34.7 mg, 0.363 mmol) and sodium ethoxide (65.4 mg, 1.21 mmol) and the resulting mixture was heated to reflux for 3 days. The reaction was cooled and concentrated in vacuo. The residue was slurried in DCM (10 mL) and water (10 mL). The undissolved solids were filtered. This material was purified by preparative reverse phase chromatography to give 57 mg (62% yield) of the title compound as a white solid. LC/MS (FA) ES+ 380, 382. 1H NMR (300 MHz, DMSO-d6) δ 8.73-8.71 (m, 2H), 8.31 (d, 1H, J=5.1 Hz), 7.88-7.86 (m, 2H), 7.36-7.30 (m, 4H), 6.86 (bs, 2H), 6.84 (d, 1H, J=5.1 Hz), 4.56 (s, 2H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 days
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. filtrationThe undissolved solids were filtered
  6. customThis material was purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-ef20b9f653ed4f23ad6977f36c27c26d
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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