Trifluoroacetic acid methylene chloride → HCID 57584956, compound

HRID 2077547Notes

Reaction equation

HRID 2077547 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][C:15]([C:17]3[CH:33]=[CH:32][C:20]4[N:21]=[C:22]([NH:24]C(=O)OC(C)(C)C)[S:23][C:19]=4[CH:18]=3)=[N:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:24][C:22]1[S:23][C:19]2[CH:18]=[C:17]([C:15]3[O:16][C:12]([NH:11][S:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)(=[O:10])=[O:9])=[N:13][N:14]=3)[CH:33]=[CH:32][C:20]=2[N:21]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57584923HCID 57584923, compound

Product 1

HCID 57584956HCID 57584956, compoundYield 94.4%

Procedure

A mixture of tert-butyl 6-(5-(4-methylphenylsulfonamido)-1,3,4-oxadiazol-2-yl)benzo[d]thiazol-2-ylcarbamate (0.40 g, 0.82 mmol) in 1:1 solution of TFA/CH2Cl2 was stirred at room temperature for 4 hours. The solution was concentrated in vacuo to give the desired product as white solid N-(5-(2-aminobenzo[d]thiazol-6-yl)-1,3,4-oxadiazol-2-yl)-4-methylbenzenesulfonamide (0.30 g, 94% yield). MS (ESI pos. ion) m/z: calc'd for C16H13N5O3S2: 387.0. found: 387.9 (MH+). 1H NMR (300 MHz, MeOH) δ ppm 2.41 (s, 3H) 7.37 (d, J=8.04 Hz, 2H) 7.54 (d, J=8.48 Hz, 1H) 7.82-7.94 (m, 3H) 8.22 (d, J=1.46 Hz, 1H).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-9558dfbbe558490f8d8cecfd14fb9221
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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