Thionyl Chloride → HCID 68455512, compound

HRID 2357634Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:16][N:15]=[CH:14]2.S(Cl)(Cl)=O.C([N:34]([CH:37]([CH3:39])[CH3:38])CC)(C)C.C1(N)CC1>C(OCC)(=O)C.O1CCOCC1>[CH:37]1([NH:34][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[N:16][N:15]=[CH:14]4)[CH:4]=2)[CH2:39][CH2:38]1

Participants

Conditions

Temperature: 65 °C

Procedure

To 4-fluoro-3-(1-morpholinophthalazin-6-yl)benzoic acid (200 mg, 566 μmol) was added thionyl chloride (2.83 mL) before it was heated to 65° C. for 1 h. The reaction mixture was concentrated in vacuo and azeotropically dried with toluene. Dioxane (2.83 mL,), diisopropylethylamine (493 μl, 2830 μmol), and cyclopropylamine (323 μl, 5660 μmol) were added and the mixture was stirred at RT overnight. The reaction mixture was diluted with 50 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 20 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound. MS (ES+): 393 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
dry with materialazeotropically dried with toluene
additionadded to a separation funnel
custompartitioned with sodium bicarbonate (saturated, aqueous)
washwashed 2 times with 20 mL of sodium bicarbonate (saturated, aqueous)
customseparated
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-47fbfc552feb444ba42c1401ffa64265
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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