Diisopropylethylamine → HCID 178480220, compound

HRID 706050Notes

Reaction equation

HRID 706050 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]2[C:13](=[O:19])[NH:14][C:15](=[S:18])[NH:16][CH:17]=2)=[CH:3]1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([O:25][C:26]2[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][C:27]=2[C:28]#[N:29])=[CH:23][C:22]=1[C:38]([F:41])([F:40])[F:39].CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([O:25][C:26]2[CH:33]=[CH:32][C:31]([CH2:34][S:18][C:15]3[NH:16][CH:17]=[C:12]([CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:2]([CH3:1])[CH:3]=4)[C:13](=[O:19])[N:14]=3)=[CH:30][C:27]=2[C:28]#[N:29])=[CH:23][C:22]=1[C:38]([F:39])([F:40])[F:41]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 677735002-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrileHCID 866662385-[(1-methyl-1H-indol-3-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

Product 1

HCID 178480220HCID 178480220, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The same procedure as E80 from 5-[(1-methyl-1H-indol-3-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (50 mg, 0.184 mmol), 2-(4-chloro-3-(trifluoromethyl) phenoxy)-5-(chloromethyl)benzonitrile (77 mg, 0.221 mmol) and DIPEA (0.097 mL, 0.553 mmol) in chloroform (2 mL) was added to afford the title compound (76 mg, 71.0% yield). LCMS: rt=3.99 min, [M+H+]=581

Sources & evidence

ORD record
ord-5b267dac25574903a1b1fb6281dc6814
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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