Acetyl chloride → HCID 86696397, compound

HRID 870694Notes

Reaction equation

HRID 870694 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]([NH:17][C:18]3[CH:32]=[CH:31][C:21]([CH2:22][NH:23]C(=O)OC(C)(C)C)=[CH:20][CH:19]=3)=[O:16])=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C>CO>[NH2:23][CH2:22][C:21]1[CH:31]=[CH:32][C:18]([NH:17][C:15]([C:12]2[N:10]3[N:11]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=[CH:8][C:9]3=[N:14][CH:13]=2)=[O:16])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86696395HCID 86696395, compound

Product 1

HCID 86696397HCID 86696397, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(6-(butylamino)imidazo[1,2-b]pyridazine-3-carboxamido)benzylcarbamate (230 mg, 0.53 mmol) in methanol (15 mL) was added acetyl chloride (0.37 mL, 5.25 mmol) dropwise. The reaction mixture was stirred for overnight, concentrated and purified by Prep HPLC (neutral) to give N-(4-(aminomethyl)phenyl)-6-(butylamino)imidazo[1,2-b]pyridazine-3-carboxamide (25 mg, 20% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.54 (s, 1H), 8.11 (s, 1H), 7.80 (d, J=8.38 Hz, 2H), 7.77 (d, J=9.92 Hz, 1H), 7.50 (d, J=8.38 Hz, 2H), 6.92 (d, J=9.70 Hz, 1H), 4.12 (s, 2H), 3.48 (t, J=7.17 Hz, 2H), 1.79 (quin, J=7.33 Hz, 2H), 1.55 (dq, J=15.02, 7.41 Hz, 2H), 1.02 (t, J=7.39 Hz, 3H); LRMS (ESI) m/e 339.2 [(M+H)+, calcd for C18H23N6O 339.4].

Workup

  1. concentrationconcentrated
  2. custompurified by Prep HPLC (neutral)

Sources & evidence

ORD record
ord-ce17a29fe145489286b270e7e84714ea
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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