Dimethylacetamide → HCID 24945977, compound

HRID 1803543Notes

Reaction equation

HRID 1803543 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].Cl.[O:15]1[CH2:21][CH2:20][CH2:19][O:18][C:17]2[C:22](NC)=[CH:23][CH:24]=[CH:25][C:16]1=2.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.[Na+].C[C:81]([N:83](C)C)=O>CCOC(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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:83][CH2:81][C:22]3[C:17]4[O:18][CH2:19][CH2:20][CH2:21][O:15][C:16]=4[CH:25]=[CH:24][CH:23]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 5

HCID 31374DimethylacetamideHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 67417425HCID 67417425, compound

Product 1

HCID 24945977HCID 24945977, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), (3,4-dihydro-2H-benzo[b][1,4]dioxepin-6-yl)-methylamine hydrochloride (140 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. (4-Chloro-6-[(3,4-dihydro-2H-benzo[b][1,4]dioxepin-6-ylmethyl)-amino]-2H-phthalazin-1-one: 52 mg (25.1%): m/z (M+H)=358. 1H-NMR (DMSO-d6) δ: 12.33 (s, 1H), 7.92 (d, 1H), 7.51 (m, 1H), 7.15 (dd, 1H), 6.97 (m, 1H), 6.89 (m, 2H), 6.83 (s, 1H), 4.38 (d, 2H), 4.17 (t, 2H), 4.11 (t, 2H), 2.12 (m, 2H).

Workup

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c073d2bb5c2242b3afdfd7f894cb2191
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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