Hydrochloric Acid → HCID 178507127, compound

HRID 1501372Notes

Reaction equation

[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:16]C)[CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-2].[Na+].[Na+].Cl.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[NH2:28][C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:8]3[N:9]=[C:10]4[CH:15]=[CH:14][C:13]([OH:16])=[N:12][N:11]4[C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:23][CH:22]=2)[CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl (1-{4-[3-phenyl-6-methoxyimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-5 (0.25 g, 0.53 mmol) in N-methylpyrrolidone (5 mL) was warmed to 100° C., then sodium sulfide (0.21 g, 2.66 mmol, 5.0 equiv) was added and the mixture was heated to 160° C. for 10 minutes. The resulting mixture was added to ice water (15 mL). The aqueous mixture was made acidic with an aqueous 2 N HCl solution, then was buffered with a saturated aqueous sodium bicarbonate solution. The resulting precipitate was removed by filtration, washed with water, and dried at 50° C. under vacuum to give 2-[4-(1-Aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-b]pyridazin-6-ol (0.10 g, 53%):

Workup

customwas prepared in a manner analgous to
temperaturethe mixture was heated to 160° C. for 10 minutes
customThe resulting precipitate was removed by filtration
washwashed with water
customdried at 50° C. under vacuum

Sources & evidence

ORD record: ord-338e01f99cdc434984e5bc8028ec6b14
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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