Riluzole → HCID 60148076, compound

HRID 512572Notes

Reaction equation

HRID 512572 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[C:37]([N:40]1[CH:44]([C:45]2[CH:46]=[CH:47][C:48]([O:56][CH3:57])=[C:49]([CH:55]=2)[O:50][CH2:51][C:52](O)=[O:53])[CH2:43][C:42]([C:58]2[CH:63]=[C:62]([O:64][CH3:65])[C:61]([O:66][CH3:67])=[C:60]([O:68][CH3:69])[CH:59]=2)=[N:41]1)(=[O:39])[CH3:38]>ClCCl.O>[F:15][C:2]([F:1])([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH:11][C:52](=[O:53])[CH2:51][O:50][C:49]3[CH:55]=[C:45]([CH:44]4[N:40]([C:37](=[O:39])[CH3:38])[N:41]=[C:42]([C:58]5[CH:63]=[C:62]([O:64][CH3:65])[C:61]([O:66][CH3:67])=[C:60]([O:68][CH3:69])[CH:59]=5)[CH2:43]4)[CH:46]=[CH:47][C:48]=3[O:56][CH3:57])[S:10][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 5070RiluzoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68279388HCID 68279388, compound

Product 1

HCID 60148076HCID 60148076, compoundYield 787.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(trifluoromethoxy)-2-aminobenzothiazole (234 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetic acid (3) (458 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25° C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (10j) (531 mg, 80% yield).

Workup

  1. extractionextracted with dichloromethane
  2. customThe solvent was evaporated under vacuum
  3. customto afford the crude product
  4. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-767b22c1d3cc4a49803535fe7f17cbfe
Source dataset
uspto-grants-2015_08
Patent number
US09102638B2

Reaction notes

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