Triethylamine → HCID 178512242, compound

HRID 1383444Notes

Reaction equation

[C:1]([NH:3][C:4](=[N:7][C:8]1[CH:13]=[CH:12]N=[CH:10][CH:9]=1)SC)#[N:2].[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C>C(O)C>[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:4]([NH:3][C:1]#[N:2])=[N:7][C:8]2[CH:13]=[CH:12][CH:27]=[C:26]3[C:9]=2[CH:10]=[CH:29][CH:28]=[N:25]3)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a reaction flask under nitrogen with magnetic stirring 1-cyano-2-methyl-3-pyridin-4-yl-isothiourea (0.35 g, 1.82 mmol) and 4-aminobenzylamine (0.25 g 2.05 mmol) were suspended in ethanol (1.5 mL). Triethylamine (0.19 g, 1.36 mmol) was added followed by (4-dimethylamino)pyridine (6 mg, 0.05 mmol). This reaction mixture was heated at 60° C. for 4 hours then cooled to room temperature. The resulting solid was collected by filtration and washed with cold ethanol (10 mL) to give N-(4-amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine as a white solid in 77% yield. 1H NMR (DMSO-d6, ppm): 9.43 (s, 1H), 8.38 (d, 2H), 8.14 (s, 1H), 7.19 (d, 2H), 7.00 (d, 2H), 6.54 (d, 2H), 5.07 (s, 2H), 4.03 (d, 2H) ESMS 289.0 (M+23).

Workup

temperaturethen cooled to room temperature
filtrationThe resulting solid was collected by filtration
washwashed with cold ethanol (10 mL)

Sources & evidence

ORD record: ord-00360c1670ff4ef29fdaf36ee32b64a9
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255323B1

Reaction notes

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