Dimethylformamide → HCID 86758812, compound

HRID 2307393Notes

Reaction equation

[C:1]([Cl:6])(=[O:5])C(Cl)=O.[Cl:7][C:8]1[CH:16]=[C:15]([C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].CN(C)C=O>O1CCCC1>[C:1]([Cl:6])([Cl:7])=[O:5].[Cl:7][C:8]1[CH:16]=[C:15]([C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

Conditions

Temperature: 35 °C

Procedure

Oxalyl chloride (0.49 ml) was added to a solution of 2-chloro-4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.41 g) from Example 114 and dimethylformamide (0.012 ml) in anhydrous tetrahydrofuran (20 ml). The reaction was heated at 35° C. for ten minutes. The resulting solution was evaporated in vacuo to dryness to yield the crude 2-chloro-4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid carbonyl chloride. Following co-evaporation with anhydrous methylene chloride, the acid chloride was dissolved in dichloromethane (20 ml) followed by the addition of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine (0.888 g) and diisopropylethylamine (1.06 ml). The resulting solution was stirred at room temperature for 2 hours. The reaction was diluted with dichloromethane and washed with water followed by 1N hydrochloric acid. The organic phase was washed with brine and dried over anhydrous magnesium sulfate. The dichloromethane was filtered and concentrated in vacuo to dryness. The residue was purified by flash column chromatography on silica pressure eluting with hexane/ethyl acetate (2/1) to afford 1.4 g of the title compound as a colorless solid m.p. 105-109° C.

Workup

customThe resulting solution was evaporated in vacuo to dryness

Sources & evidence

ORD record: ord-5857adf372ed423a84440f8fc396cd6d
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831079B1

Reaction notes

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