4-Aminomethyl-4'-fluoro-biphenyl-2-ol → 4-[[[4-(4-fluorophenyl)-3-hydroxyphenyl]methylamino]methylidene]-6-(furan-2-yl)isoquinoline-1,3-dione

HRID 2236869Notes

Reaction equation

HRID 2236869 reaction equation
OC1C=C(CNC=C2C3C(=CC=C(I)C=3)C(=O)NC2=O)C=CC=1C1C=CC=CC=1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[C:41](=[O:45])[NH:40][C:39](=[O:46])[C:38]2=[CH:47]OC.[NH2:50][CH2:51][C:52]1[CH:53]=[C:54]([OH:65])[C:55]([C:58]2[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=2)=[CH:56][CH:57]=1>>[F:64][C:61]1[CH:62]=[CH:63][C:58]([C:55]2[CH:56]=[CH:57][C:52]([CH2:51][NH:50][CH:47]=[C:38]3[C:37]4[C:42](=[CH:43][CH:44]=[C:35]([C:31]5[O:30][CH:34]=[CH:33][CH:32]=5)[CH:36]=4)[C:41](=[O:45])[NH:40][C:39]3=[O:46])=[CH:53][C:54]=2[OH:65])=[CH:59][CH:60]=1

Participants

4

Reactant 3

HCID 592999224-Aminomethyl-4'-fluoro-biphenyl-2-olHCID 686963676-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dioneHCID 178518360HCID 178518360, compound

Product 1

HCID 1785183004-[[[4-(4-fluorophenyl)-3-hydroxyphenyl]methylamino]methylidene]-6-(furan-2-yl)isoquinoline-1,3-dioneYield 62%

Procedure

Following the same procedure for the preparation of 4-{[(2-Hydroxy-biphenyl-4-ylmethyl)-amino]-methylene}-6-iodo-4H-isoquinoline-1,3-dione, the title compound is prepared from 6-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dione (40 mg, 0.15 mmol) and 4-Aminomethyl-4′-fluoro-biphenyl-2-ol (33 mg, 0.15 mmol) in 62% yield: MS (ESI): 453.2 (M−1)−1.

Sources & evidence

ORD record
ord-ca14147dd53e48a8a26c730629cbc0cc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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