1-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetate → 2-(2,6-Dichloro-phenylamino)-1,6-dimethyl-7-[3-(4-oxo-4-phenyl-4lambda5-[1,4]azaphosphinan-1-yl)-propenyl]-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

HRID 1863906Notes

Reaction equation

HRID 1863906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:32])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23](OC(=O)C)[CH:24]=[CH2:25])=[C:17]([CH3:30])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:31]=1.[C:33]1([P:39]2(=[O:45])[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:32])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]=[CH:24][CH2:25][N:42]4[CH2:41][CH2:40][P:39](=[O:45])([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH2:44][CH2:43]4)=[C:17]([CH3:30])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:31]=1

Participants

3

Reactant 2

HCID 108743751-[2-(2,6-dichloroanilino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]allyl acetateHCID 579259574-Phenyl-1,4lambda5-azaphosphinan-4-one

Product 1

HCID 668324662-(2,6-Dichloro-phenylamino)-1,6-dimethyl-7-[3-(4-oxo-4-phenyl-4lambda5-[1,4]azaphosphinan-1-yl)-propenyl]-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

Procedure

2-(2,6-Dichloro-phenylamino)-1,6-dimethyl-7-[3-(4-oxo-4-phenyl-4λ5-[1,4]azaphosphinan-1-yl)-propenyl]-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one was prepared following the procedure of Example 1 form acetic acid 1-[2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinolin-7-yl]-allyl ester and 4-phenyl-[1,4]azaphosphinane 4-oxide. 1HNMR (400 MHz, DMSO-d6+TFA) δ 11.38 (br s, 1H), 10.71 (br s, 1H), 7.90-7.60 (m, 9H), 7.56 (t, 1H, J=7.8 Hz), 7.22 (br d, 1H, J=15.3 Hz), 7.70-6.40 (br m, 1H), 4.23 (s, 3H), 4.18 (br m, 2H), 4.00 -4.15 (br m, 4H), 2.60-2.40 (br n, 4H), 2.39 (s, 1H); ESMS (m/z): found, 606 (M+1)+.

Sources & evidence

ORD record
ord-b1525394e73e4d798752c19b0c7b8bfc
Source dataset
uspto-grants-2009_12
Patent number
US07625880B2

Reaction notes

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