Hydrochloric Acid → HCID 178513492, compound

HRID 64319Notes

Reaction equation

[C:1]([N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]3[N:13]([N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:21]=4)[C:16]=3[C:17]([NH2:19])=[O:18])[C:7]=2[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].O1CCOCC1.[ClH:39]>>[Cl:39][CH2:3][CH2:2][C:1]([N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]3[N:13]([N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:21]=4)[C:16]=3[C:17]([NH2:19])=[O:18])[C:7]=2[CH2:6]1)=[O:4]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 178459953HCID 178459953, compound

Product 1

HCID 178513492HCID 178513492, compoundYield 90%

Procedure

7-Acryloyl-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5′,1′:2,3]imidazo[4,5-c]pyridine-3-carboxamide (40 mg, 0.09 mmol) was suspended in Sat. HCl (gas)/dioxane (50 mL), then the mixture was stirred RT for about 1.5 hr, and concentrated to dryness. The residue was suspended into 2 mL of MeOH and 2 mL of water. The organic layer was discarded, aqueous layer was lyophilized to get 40 mg (90%) of 7-(3-chloropropanoyl)-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5′,1′:2,3]imidazo[4,5-c]pyridine-3-carboxamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.79-11.76 (m, 1H), 7.68 (d, J=8.6 Hz, 2H), 7.43 (d, J=7.6 Hz, 1H), 7.41 (d, J=7.6 Hz, 1H), 7.18 (t, J=7.6 Hz, 1H), 7.10-7.04 (m, 4H), 4.71-4.70 (m, 2H), 3.85-3.79 (m, 4H), 3.02 (t, J=6.4 Hz, 2H), 2.79-2.69 (m, 2H). MS (ESI) m/e [M+1]+ 463.8, 465.8.

Workup

concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-258b4ddc41734336801def1426025538
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Reaction notes

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