Acetyl chloride → HCID 86696385, compound

HRID 870682Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)(C)(C)C.C(Cl)(=[O:39])C>>[C:14]([OH:35])(=[O:39])[CH3:15].[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:35])[CH2:12][CH2:13]1

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 86696384HCID 86696384, compound

Product 1

HCID 86696385HCID 86696385, compoundYield 150.3%

Procedure

The solution of tert-butyl(1-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperidin-4-yl)carbamate (47 mg, 0.1 mmol) was cooled to 0° C. and treated with acetyl chloride (225 mg, 2.86 mmol). The reaction was maintained at room temperature for overnight. The resulting solution was concentrated under reduced pressure and the residue was purified by preparative HPLC (neutral) to afford (4-aminopiperidin-1-yl)(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)phenyl)methanone acetic acid salt (34 mg, 79% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.17-8.42 (m, J=8.3 Hz, 2H), 7.86 (s, 1H), 7.63 (d, J=9.6 Hz, 1H), 7.48-7.57 (m, J=8.6 Hz, 2H), 6.74 (d, J=9.6 Hz, 1H), 3.36-3.49 (m, 3H), 1.90-1.99 (m, 9H), 1.72 (quin, J=7.3 Hz, 2H), 1.63 (br. s., 2H), 1.44-1.55 (m, 2H), 1.01 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 393.2 [(M+H)+, calcd for C22H29N6O 393.2].

Workup

concentrationThe resulting solution was concentrated under reduced pressure
customthe residue was purified by preparative HPLC (neutral)

Sources & evidence

ORD record: ord-3f2fee59eacb47249846b594d1b6d311
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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