Thionyl Chloride → HCID 57929981, compound

HRID 1930017Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:30][CH2:29][CH2:28][N:12]2[C:13]=1[C:14]1[N:19]=[N:18][C:17]([NH:20][NH:21][C:22]([C:24]2([CH3:27])[CH2:26][CH2:25]2)=O)=[CH:16][CH:15]=1.S(Cl)(Cl)=O>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:30][CH2:29][CH2:28][N:12]2[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:22]([C:24]3([CH3:27])[CH2:26][CH2:25]3)=[N:21][N:20]=2)[N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 125 mL flask was charged with N′-(6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)pyridazin-3-yl)-1-methylcyclopropanecarbohydrazide (0.458 g, 0.614 mmol, prepared using General Procedure AR from Example #35, Step E with 1-methylcyclopropanecarboxylic acid) and 1,4-dioxane (20 mL) to give a brown suspension. To the suspension, thionyl chloride (0.3 mL, 4.11 mmol) was added and the mixture was stirred at about 80° C. After about 4 h, the reaction was concentrated under reduced pressure. The residue was redissolved in DCM and washed with saturated aqueous Na2CO3. The organic solution was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel chromatography using MeOH/DCM (gradient; 0:100 to 10:90) to give the title compound (0.140 g, 58% yield): LC/MS (Table 1, Method a) Rt=2.28 min; MS m/z: 393.3 (M+H)+.

Workup

customto give a brown suspension
concentrationthe reaction was concentrated under reduced pressure
dissolutionThe residue was redissolved in DCM
washwashed with saturated aqueous Na2CO3
dry with materialThe organic solution was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-7b544af71cd143c584aadea06d4a0861
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

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