Sodium ethoxide → HCID 178508353, compound

HRID 78606Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:14]([NH:16][NH2:17])=O)=[N:4][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][N:7]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](N)=[NH:24].C([O-])C.[Na+]>CN(C=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[N:4]=[C:3]([C:14]3[NH:24][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[N:17][N:16]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

3-amino-6-(3-pyridyl)pyrazine-2-carbohydrazide (40 mg, 0.173 mmoles), thiophene-2-carboxamidine (21.92 mg, 0.173 mmoles) and sodium ethanolate (11.82 mg, 0.173 mmoles) were added to a microwave vial. DMF (1 mL) was then added and the vial sealed and heated in the microwave at 160° C. for 40 minutes. The reaction mixture was filtered and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (23.4 mg, 31% Yield). 1H NMR (400.0 MHz, DMSO-d6) d 14.96 (s, 1H), 9.55 (s, 1H), 8.99 (s, 1H), 8.84 (d, J=6.1 Hz, 1H), 8.69 (dd, J=1.2, 4.9 Hz, 1H), 7.95 (s, 2H), 7.81 (d, J=3.0 Hz, 1H), 7.73-7.68 (m, 2H) and 7.22 (dd, J=3.8, 4.8 Hz, 1H) ppm; MS (ES+) 323.10

Workup

customthe vial sealed
filtrationThe reaction mixture was filtered
custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
customThe fractions were collected
customfreeze-dried

Sources & evidence

ORD record: ord-33886daa9fbe44b29837b4492acd5e67
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841308B2

Reaction notes

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