Acetic Acid → HCID 86696417, compound

HRID 870715Notes

Reaction equation

[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:31]=[CH:30][C:18]([C:19]([NH:21][CH2:22][CH:23]4[CH2:27][O:26]C(C)(C)[O:24]4)=[O:20])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].CC(O)=O>O>[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:31]=[CH:30][C:18]([C:19]([NH:21][CH2:22][CH:23]([OH:24])[CH2:27][OH:26])=[O:20])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To 150 mg (0.355 mmol) of 4-(6-butylamino-imidazo[1,2-b]pyridazin-3-yl)-N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-benzamide was added 15 ml of AcOH and 5 mL of water and heated to 60° C. for 1.5 hr. It was concentrated and the crude was purified on the acetic PREP HPLC to yield 107 mg (79%) of the titled compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.00 (t, J=7.39 Hz, 3H) 1.42-1.55 (m, 2H) 1.66-1.76 (m, 2H) 3.40 (t, J=7.17 Hz, 2H) 3.43-3.52 (m, 1H) 3.56-3.65 (m, 3H) 3.84-3.93 (m, 1H) 7.24 (d, J=9.92 Hz, 1H) 7.96 (d, J=9.92 Hz, 1H) 8.00-8.05 (m, 2H) 8.23-8.28 (m, 2H) 8.30 (s, 1H); LRMS (ESI) m/e 384.0 [(M+H)+, calcd for C20H25N5O3 383.0]

Workup

concentrationIt was concentrated
customthe crude was purified on the acetic PREP HPLC

Sources & evidence

ORD record: ord-9bd46c74d2ab4ee892465fe3ab6248ed
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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