Trifluoroacetic acid → HCID 89761701, compound

HRID 528628Notes

Reaction equation

HRID 528628 reaction equation
COC1C=CC(C[N:8]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[CH:28]=[N:29][CH:30]=[N:31][CH:32]=4)[CH2:19][CH2:18][O:17][C:16]=3[CH:33]=2)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:29]1[CH:28]=[C:27]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]2[CH2:19][CH2:18][O:17][C:16]3[CH:33]=[C:12]([S:9]([NH:8][C:34]4[S:35][CH:36]=[CH:37][N:38]=4)(=[O:10])=[O:11])[CH:13]=[CH:14][C:15]2=3)[CH:32]=[N:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761875HCID 89761875, compound

Product 1

HCID 89761701HCID 89761701, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (250 mg, 0.437 mmol) in DCM (5 mL) was added TFA (2 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h. After completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (8 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material (69.61% by LCMS) that was purified by prep purification to obtain 4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (60 mg, 30.4%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 9.06 (s, 1H), 8.83 (s, 2H), 7.61 (td, J=6.9, 2.0 Hz, 2H), 7.58-7.48 (m, 2H), 7.21 (d, J=4.7 Hz, 1H), 7.01 (td, J=4.8, 4.2, 1.8 Hz, 2H), 6.77 (d, J=4.7 Hz, 1H), 6.21 (d, J=9.0 Hz, 1H), 4.30 (dt, J=11.1, 3.2 Hz, 1H), 4.03 (ddd, J=10.9, 8.6, 2.7 Hz, 1H), 3.76 (ddd, J=11.3, 8.3, 3.0 Hz, 1H), 3.44 (dt, J=12.3, 3.1 Hz, 1H); MS (ESI, positive ion) m/z: 452.1 (M+1).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (8 mL)
  2. extractionextracted with DCM (2×10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude material (69.61% by LCMS) that
  6. customwas purified by prep purification

Sources & evidence

ORD record
ord-a4182293a81b4036b000b9697885faa7
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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