Triethylamine → HCID 57465132, compound

HRID 1170874Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:5])[CH3:2].C(N(CC)CC)C.[F:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[F:37])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:36]([F:37])=[C:28]([F:27])[CH:29]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound F (3.2 g, 12.1 mmol) and triethylamine (2.54 mL, 18.1 mmol, 1.5 eq.) were dissolved in DCM (70 mL) and the solution was cooled to 0° C. 3,4-difluorobenzoylchloride (1.66 mL, 13.3 mmol, 1.1 eq.) was added dropwise. After 90 minutes the reaction mixture was diluted with DCM (130 mL) and washed with 0.5 M KHSO4 in water (200 mL), saturated aqueous NaHCO3 solution (200 mL) and saturated aqueous NaCl solution (200 mL). The combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum and the untreated product 2-[butyl-(3,4-difluoro-benzoyl)-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester was used directly in the next stage.

Workup

washwashed with 0.5 M KHSO4 in water (200 mL), saturated aqueous NaHCO3 solution (200 mL) and saturated aqueous NaCl solution (200 mL)
dry with materialThe combined organic phases were dried over sodium sulphate
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-62d6918a96de4309893efef738cdc743
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829568B2

Reaction notes

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