Triethylamine → HCID 71555128, compound

HRID 2281687Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:10]([CH2:11][NH:12]2)[CH2:9]1)=[O:7].Br[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(CC)CC)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:10]([CH2:11][N:12]2[C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:9]1)=[O:7]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of rac-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylic acid 2,4-dichloro-benzylamide (150 mg, 270 μmol) in toluene (6 mL) were added 2-bromopyrimidine (43 mg, 270 μmol) and triethylamine (27 mg, 270 μmol). After addition of tris(dibenzylideneacetone)dipalladium(0) (5 mg, 5 μmol), BINAP (10 mg, 16 μmol) and potassium tert-butylate (30 mg, 270 μmol) the reaction mixture was heated under an argon atmosphere to 110° C. for 20 h. It was filtered and concentrated in vacuo. Purification by chromatography (SiO2; dichloromethane:methanol 1:0 to 9:1) afforded the title compound (26 mg, 25%) as a white solid. MS (EI) m/e: 378.3 (M+H)+.

Workup

filtrationIt was filtered
concentrationconcentrated in vacuo
customPurification by chromatography (SiO2; dichloromethane:methanol 1:0 to 9:1)

Sources & evidence

ORD record: ord-6e559ee3ad8340a7b4ea4583d845bd4d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139593B2

Reaction notes

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