Binap, (A+-)- → HCID 24948152, compound

HRID 1667495Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[CH:7]=[CH:8][CH:9]=1.Br[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[NH:23][N:22]=[C:21]2[Cl:29].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+]>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].CC(N(C)C)=O>[Cl:29][C:21]1[C:20]2[C:25](=[CH:26][CH:27]=[C:18]([NH:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[CH:5]=3)[CH:19]=2)[C:24](=[O:28])[NH:23][N:22]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-(3-aminomethyl-phenyl)-N′,N′-dimethyl-propane-1,3-diamine hydrochloride (65 mg, 0.267 mmol), 6-bromo-4-chloro-2H-phthalazin-1-one (66 mg, 0.254), Pd2(dba)3 (31 mg, 0.0339 mmol), rac-BINAP (57 mg, 0.0915 mmol), NaOtBu (88 mg, 0.916 mmol) and DMA (5 mL) was heated to 85° C. until the reaction was completed by HPLC. The reaction was filtered through celite and purified by preparatory HPLC to yield 4-chloro-6-[3-(3-dimethylamino-propylamino)-benzylamino]-2H-phthalazin-1-one hydroformate (17 mg) as an orange solid. 1H (400 MHz, d6-DMSO) δ: 1.62 (quintet, 2H), 2.11 (s, 6H), 2.26 (t, 2H), 2.98 (t, 2H), 4.29 (d, 2H), 6.42 (d, 1H), 6.53 (m, 2H), 6.81 (s, 1H), 7.10 (t, 1H), 7.12 (dd, 1H), 7.60 (t, 1H), 7.91 (d, 1H), 8.20 (s, 2H), 12.32 (s, 1H) ppm; m/z (M+1) 385.96.

Workup

filtrationThe reaction was filtered through celite
custompurified by preparatory HPLC

Sources & evidence

ORD record: ord-0c09acbea9da4ba28fbd5407575850de
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044041B2

Reaction notes

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