Dimethylacetamide → HCID 131729241, compound

HRID 1667535Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24](C2C=CC=CC=2CN)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=CC(P([C:49]2[C:58]([C:59]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=[C:57]3[C:52](C=CC=C3)=[CH:51][CH:50]=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].CC([N:91](C)C)=O>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]>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:57]1[CH:52]=[CH:51][CH:50]=[CH:49][C:58]=1[CH2:59][NH:91][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13])=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-bromo-4-chloro-2H-phthalazin-1-one (140 mg, 0.54 mmol), 4-(2-Aminomethyl-phenyl)-perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (150 mg, 0.49 mmol), Pd2(dba)3 (45 mg, 0.049 mmol), BINAP (92 mg, 0.15 mmol) and NaOt-Bu (138 mg, 1.47 mmol) in DMA (10 mL) was purged with nitrogen for 10 min. The mixture was heated at 90° C. for 5 h. The mixture was allowed to cool and diluted with ethyl acetate (30 mL) and washed with ammonium chloride (25 mL). The organic layer was dried and concentrated. Chromatography on silica yielded the title compound (25 mg, 11%) m/z (M+H)=484.72.

Workup

customwas purged with nitrogen for 10 min
temperatureto cool
additiondiluted with ethyl acetate (30 mL)
washwashed with ammonium chloride (25 mL)
customThe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-0763c4711c7848f9ba6c85bda5b2e3e9
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044041B2

Reaction notes

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