Guanidine Hydrochloride → HCID 178508871, compound

HRID 2059760Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].O=[C:7]1[CH:18]([C:19](OC)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][C:8]21[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:4][C:3]1[N:5]=[C:19]([OH:20])[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[C:7]=2[N:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of guanidine hydrochloride (430 mg, 4.5 mmol), the product from Example 16B (430 mg, 1.8 mmol), and potassium carbonate (623 mg, 4.5 mmol) in DMF (8 mL) was heated at 100° C. for 16 hours. Then, the temperature was raised to 120° C. for 2 hours. The mixture was cooled to ambient temperature and filtered through a layer of diatomaceous earth, then the filter pad was washed with a small amount of DMF. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel (10:45:45 MeOH/CH2Cl2/EtOAc, eluant) to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) ppm 10.62 (s, 1 H), 6.04 (s, 2 H), 2.57-2.64 (m, 2 H), 1.93-2.05 (m, 2 H), 1.60-1.71 (m, 4 H), 1.35-1.57 (m, 9 H), 1.15-1.28 (m, 1 H). MS (DCI+) m/z 248 (M+H).

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationfiltered through a layer of diatomaceous earth
washthe filter pad was washed with a small amount of DMF
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was chromatographed on silica gel (10:45:45 MeOH/CH2Cl2/EtOAc, eluant)

Sources & evidence

ORD record: ord-20a112029c3144edba1b63335cd378cf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278313B2

Reaction notes

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