Water → HCID 86696415, compound

HRID 870713Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[N:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH2:7][NH:8][C:9](=O)[C:10](F)(F)F)[CH3:2].[Br:22][C:23]1[N:27]2[N:28]=C(F)C=[CH:31][C:26]2=[N:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC>[CH2:1]([O:3][C:4](=[O:21])[N:5]([CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[CH:31][C:26]2[N:27]([C:23]([Br:22])=[CH:24][N:25]=2)[N:28]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

Crude phenyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-carbamic acid ethyl ester (2.2 g, 7.3 mmol) was combine with 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (892.5 mg, 4.1 mmol) and potassium carbonate [584-08-7] (2.9 g, 20.6 mmol) in a 20% (v/v) solution of water in 1,2-dimethoxyethane (25 mL) and heated to 85° C. for 5 d. The reaction mixture was then partitioned between water and ethyl acetate and the extract flash chromatographed (silica gel eluted with 100% ethyl acetate) to yield 863.1 mg of white crystalline powder, mp. 160-161° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (t, J=7.06 Hz, 2H) 2.51 (dt, J=3.58, 1.85 Hz, 1H) 3.35 (s, 1H) 3.46 (q, J=6.39 Hz, 2H) 3.90 (t, J=6.50 Hz, 2H) 4.04 (q, J=7.06 Hz, 2H) 6.65 (d, J=9.70 Hz, 1H) 7.19-7.25 (m, 1H) 7.31-7.39 (m, 4H) 7.48 (s, 1H) 7.69 (d, J=9.70 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 14.16, 38.85, 47.84, 60.82, 98.79, 112.62, 125.31, 125.99, 126.79, 128.63, 130.18, 136.35, 141.81, 153.79, 154.64. LRMS (ESI) m/z 403.9/405.9 [(M+H)]+, calc'd for C17H18BrN6O2: 404.27.

Workup

customThe reaction mixture was then partitioned between water and ethyl acetate
customthe extract flash chromatographed
wash(silica gel eluted with 100% ethyl acetate)

Sources & evidence

ORD record: ord-2da7c5eb50bf4131b202749fb4ddda8a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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