Trifluoroacetic acid → HCID 71556741, compound

HRID 920226Notes

Reaction equation

HRID 920226 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:39]1[S:43][N:42]=[CH:41][N:40]=1)[S:7]([C:10]1[C:37]([F:38])=[CH:36][C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3/[CH:25]=[CH:26]/[CH2:27][NH:28]C(=O)OC(C)(C)C)[C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][CH2:27]/[CH:26]=[CH:25]/[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:14]1[C:13]2[CH:36]=[C:37]([F:38])[C:10]([S:7]([NH:6][C:39]3[S:43][N:42]=[CH:41][N:40]=3)(=[O:9])=[O:8])=[CH:11][C:12]=2[O:16][C:15]1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117638086HCID 117638086, compound

Product 1

HCID 71556741HCID 71556741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Formula 12-2 thus prepared (125 mg, 0.176 mmol) was placed into a 1 dram vial containing 702 μL of DCM and 176 μL of TFA at ambient temperature (RT). After 20 minutes of stirring at RT, LCMS indicated complete consumption of was placed 125 mg of 12-2. The reaction mixture was concentrated in vacuo, dissolved in MeOH (1 mL), filtered and purified by reverse-phase HPLC (5-60% MeCN in water with 0.1% TFA, C18 column) to give 12-3 (3-{2-[(1E)-3-Aminoprop-1-en-1-yl]benzyl}-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide) as a white solid. 1H NMR δ (ppm)(DMSO-d6): 8.40 (1H, s), 7.95 (2H, br s), 7.77 (1H, d, J=5.32 Hz), 7.50 (1H, d, J=7.71 Hz), 7.35 (1H, t, J=7.54 Hz), 7.28 (1H, t, J=7.56 Hz), 7.21 (3H, t, J=7.71 Hz), 7.09 (2H, d, J=12 Hz), 6.16-6.09 (2H, m), 5.12 (2H, s). HRMS C19H17FN5O4S2 [M+H] calc 462.0701, obs 462.0706.

Workup

  1. customconsumption
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in MeOH (1 mL)
  4. filtrationfiltered
  5. custompurified by reverse-phase HPLC (5-60% MeCN in water with 0.1% TFA, C18 column)

Sources & evidence

ORD record
ord-498559fc802d46808c412165a24404e2
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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