Hydrochloric Acid → HCID 178490957, compound

HRID 1943493Notes

Reaction equation

[CH:1]1([N:4]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:5]2[C:6]3[N:7]([C:26]([C:29](=[O:38])NC4C=CN=CC=4F)=[CH:27][N:28]=3)[N:8]=[C:9]([NH:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:13]3)[CH:10]=2)[CH2:3][CH2:2]1.[OH-:48].[Na+].Cl>CO>[C:21]([O:20][C:19]([NH:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([NH:11][C:9]2[CH:10]=[C:5]([N:4]([CH:1]3[CH2:3][CH2:2]3)[CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[C:6]3[N:7]([C:26]([C:29]([OH:48])=[O:38])=[CH:27][N:28]=3)[N:8]=2)[CH2:17][CH2:16]1)=[O:25])([CH3:22])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 65 °C

Procedure

83B (19 mg, 0.029 mmol) was dissolved in MeOH (1 mL). 0.5 mL of 1N NaOH was added, and the cloudy reaction mixture was stirred at 65° C. After 2 hrs, the reaction mixture was cooled to room temperature, the pH adjusted to pH 7 with 1N HCl, and the solid was collected via Buchner filtration to afford 6-((trans)-4-(tert-butoxycarbonylamino)cyclohexylamino)-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid as a white solid (10.6 mg, 0.019 mmol, 65.3% yield). LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA) Rt=2.1 minutes. [M+H]=551.36.

Workup

customthe cloudy reaction mixture
temperaturethe reaction mixture was cooled to room temperature
filtrationthe solid was collected via Buchner filtration

Sources & evidence

ORD record: ord-a23ced91ca794195b1ba95f4b1e9a8ca
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389527B2

Reaction notes

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