Hydrochloric Acid → HCID 178479645, compound

HRID 541805Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[C:17](Cl)[N:16]=2)[CH:9]=1)=[O:6].Cl>COCCO.O1CCOCC1>[ClH:21].[Cl:21][C:20]1[CH:19]=[N:18][C:17]2[NH:1][C:2]3[CH:25]=[CH:24][CH:23]=[C:4]([CH:3]=3)[C:5](=[O:6])[NH:7][C:8]3[CH:9]=[C:10]([NH:14][C:15]=1[N:16]=2)[CH:11]=[CH:12][CH:13]=3

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}benzamide (20.0 mg, 0.053 mmol) in 2-methoxyethanol (0.295 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (67 μL). The resulting mixture was heated at 150° C. in a microwave for 15 min. After filtration of the reaction mixture, the crude was triturated with MeOH/EtOAc to give the desired product as an off-white powder (12 mg, 66%). LCMS for C17H12ClN5O (M+H)+: m/z=337.9. 1H NMR (400 MHz, DMSO-d6): δ 10.32 (s, 1H), 10.16 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 9.66 (ddd, J=7.6, 2.0, 1.2 Hz, 1H), 9.38 (s, 1H), 6.30 (br, 1H), 8.24 (m, 1H), 7.38 (ddd, J=8.0, 2.0, 1.2, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.25 (m, 2H), 7.16 (m, 1H), 6.95 (t, J=2.0 Hz, 1H).

Workup

filtrationAfter filtration of the reaction mixture
customthe crude was triturated with MeOH/EtOAc

Sources & evidence

ORD record: ord-1291adb91aae44beaa0843b20f0d3dfb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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