Dimethylformamide → (R)-4-{4-[2-(4-Fluoro-1H-indol-1-yl)propionyl]piperazin-1-yl}-N-[1,2,4]thiadiazol-5-yl benzenesulfonamide

HRID 2043110Notes

Reaction equation

HRID 2043110 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[S:21][N:20]=[CH:19][N:18]=3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6]CNC[CH2:2]1.CN(C(ON1N=N[C:32]2[CH:33]=CC=N[C:31]1=2)=[N+](C)C)C.[F:39][P-](F)(F)(F)(F)F.[CH:46]([N:49]([CH2:53][CH3:54])[CH:50]([CH3:52])[CH3:51])([CH3:48])C.[CH3:55][N:56]([CH:58]=[O:59])[CH3:57]>C(Cl)Cl>[F:39][C:33]1[CH:32]=[CH:31][CH:51]=[C:50]2[C:52]=1[CH:48]=[CH:46][N:49]2[C@H:53]([CH3:54])[C:58]([N:56]1[CH2:57][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]3[S:21][N:20]=[CH:19][N:18]=3)(=[O:14])=[O:15])=[CH:11][CH:12]=2)[CH2:6][CH2:55]1)=[O:59]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594660734-(piperazin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Product 1

HCID 59465923(R)-4-{4-[2-(4-Fluoro-1H-indol-1-yl)propionyl]piperazin-1-yl}-N-[1,2,4]thiadiazol-5-yl benzenesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized according to general procedure 5, method B. The reaction was set up with 0.61 mmol 4-(piperazin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide, 0.61 mmol(2R)-2-(4-fluoro-indol-1-yl)-propionic acid, 0.61 mmol HATU, 0.61 mmol N,N-diisopropyl ethyl amine and 2 mL (1:1) DMF:methylene dichloride to get (R)-4-{-4-[2-(4-Fluoro-1H-indol-1-yl)propionyl]piperazin-1-yl}-N-[1,2,4]thiadiazol-5-yl benzenesulfonamide as a white solid (200 mg, 63% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=515.3; tR=3.16 min. 1H NMR (400 MHz, DMSO-d6) δ 8.16 (s, 1H), 7.56 (d, J=9.0 Hz, 2H), 7.47 (s, 1H), 7.37 (s, 1H), 7.15-7.09 (m, 1H), 6.94 (d, J=9.1 Hz, 2H), 6.84-6.79 (m, 1H), 6.54 (d, J=3.2 Hz, 1H), 5.87-5.82 (m, 1H), 3.66 (d, J=4.6 Hz, 2H), 3.58-3.53 (m, 2H), 3.17-3.09 (m, 4H), 1.59 (s, 3H).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b1ef4db9ceea4f498aaf40d996aa28fb
Source dataset
uspto-grants-2013_11
Patent number
US08586589B2

Reaction notes

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