HCID 68938761, compound → HCID 73320822, compound

HRID 2191246Notes

Reaction equation

O=C1C(=[C:11]([C:14]#[N:15])[C:12]#[N:13])C2C(=CC=C(S(N3CCCC3COC3C=CC=CC=3)(=O)=O)C=2)N1.[OH:32][C:33]1[CH:66]=[CH:65][C:36]([CH2:37][N:38]2[C:46]3[C:41](=[CH:42][C:43]([S:47]([N:50]4[CH2:54][CH2:53][CH2:52][CH:51]4[CH2:55][O:56][C:57]4[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=4)(=[O:49])=[O:48])=[CH:44][CH:45]=3)[C:40](=O)[C:39]2=[O:64])=[CH:35][CH:34]=1>>[OH:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][N:38]2[C:46]3[C:41](=[CH:42][C:43]([S:47]([N:50]4[CH2:54][CH2:53][CH2:52][CH:51]4[CH2:55][O:56][C:57]4[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=4)(=[O:49])=[O:48])=[CH:44][CH:45]=3)[C:40](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[C:39]2=[O:64])=[CH:65][CH:66]=1

Participants

Reactant 2

HCID 68938761HCID 68938761, compound

HCID 73320783HCID 73320783, compound

Product 1

HCID 73320822HCID 73320822, compoundYield 85%

Procedure

2-{1-(4-Hydroxy-benzyl)-2-oxo-5-[2-(pyridine-3-yloxymethyl)-pyrrolidine-1-sulfonyl]-1,2-dihydro-indol-3-yl-idene}-malononitrile (30b) was prepared according to the same procedure for compound 26 except using 28b, to afford 46 mg (85%) of 30b as a purple solid, mp 203.3° C. (decomp). 1H NMR (300 MHz, DMSO) δ 9.50 (s, 1H), 8.31 (s, 1H), 8.25 (d, J=2.7 Hz, 1H), 8.17 (dd, J=4.5 Hz, J=1.5 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 7.34 (m, 3H), 7.24 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.7 Hz, 2H), 4.88 (s, 2H), 4.16 (m, 1H), 4.08 (m, 1H), 3.96 (m, 1H), 3.41 (m, 1H), 3.18 (m, 1H), 1.91 (m, 2H), 1.71 (m, 2H).

Workup

custom2-{1-(4-Hydroxy-benzyl)-2-oxo-5-[2-(pyridine-3-yloxymethyl)-pyrrolidine-1-sulfonyl]-1,2-dihydro-indol-3-yl-idene}-malononitrile (30b) was prepared

Sources & evidence

ORD record: ord-307f401168b844149950ba92b8c60506
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329686B2

Reaction notes

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