Hydrochloric Acid → HCID 89650338, compound

HRID 2174247Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)[C:10]([C:24](=[O:32])[NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:9][N:8]=1)=[O:5])[CH3:2].O.[OH-].[Na+].Cl>C(#N)C>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=2)[C:10]([C:24](=[O:32])[NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:9][N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 4-[[2-(ethylcarbamoylamino)-5-(3-pyridylcarbamoyl)-4-pyridyl]amino]benzoate (35 mg, 0.07 mmol) was suspended in acetonitrile (3 mL) and water (3 mL) and treated with NaOH (1 mL, 1 M). The mixture was heated to 40° C. for 40 minutes. The mixture was adjusted to pH ˜6 by addition of dilute aqueous HCl. The mixture was then freeze-dried. The crude product was dissolved in DMSO/water and purified by reverse phase chromatography (12 g Reveleris C18 cartridge, eluting with 0-100% acetonitrile in 0.1% aqueous formic acid). Compound 16 was isolated as a white solid (23 mg, 68%). 1H NMR (400 MHz, DMSO-d6): δ 10.53 (s, 1H), 10.04 (s, 1H), 9.24 (s, 1H), 8.86 (d, J=2.1 Hz, 1H), 8.64 (s, 1H), 8.32 (dd, J=4.7, 1.5 Hz, 1H), 8.12 (ddd, J=8.4, 2.5, 1.5 Hz, 1H), 7.93 (d. J=8.7 Hz, 2H), 7.87 (s, 1H), 7.51 (s, 1H), 7.40 (ddd, J=8.4, 4.7, 0.6 Hz, 1H), 7.36 (d. J=8.8 Hz, 2H), 3.20-3.12 (m, 2H), 1.07 (t, J=7.2 Hz, 3H). [M+H]+ m/z=421.14.

Workup

customThe mixture was then freeze-dried
dissolutionThe crude product was dissolved in DMSO/water
custompurified by reverse phase chromatography (12 g Reveleris C18 cartridge, eluting with 0-100% acetonitrile in 0.1% aqueous formic acid)

Sources & evidence

ORD record: ord-dc5044bb2fc9448e860d0961fc1b86a5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09060515B2

Reaction notes

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