N-bromobutanimide → 2-Bromo-4-(1,1-dioxo-1lambda6[1,2,6]thiadiazinan-4-yl)-phenylamine

HRID 930144Notes

Reaction equation

HRID 930144 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][NH:18][S:17](=[O:21])(=[O:20])[NH:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.C1C(=O)N([Br:30])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:30][C:9]1[CH:10]=[C:11]([CH:14]2[CH2:19][NH:18][S:17](=[O:21])(=[O:20])[NH:16][CH2:15]2)[CH:12]=[CH:13][C:8]=1[NH2:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59771229[4-(1,1-Dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 597711772-Bromo-4-(1,1-dioxo-1lambda6[1,2,6]thiadiazinan-4-yl)-phenylamineYield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[4-(1,1-Dioxo-1λ6-[1,2,6]thiadiazinan-4-yl)-phenyl]-carbamic acid tert-butyl ester (as prepared in the previous step, 100 mg, 0.305 mmol) was dissolved in TFA (1 mL). The resulting solution was stirred at RT for 30 min and concentrated in vacuo. The residue obtained (74.3 mg) was dried in vacuo for 1 h and dissolved in HOAc (2 mL). The resulting mixture was cooled to 0° C. and NBS (42.6 mg, 0.239 mmol) was added. The resulting mixture was stirred for 30 min, washed with aq NaHCO3 (2 mL) and concentrated. The residue was purified on silica (20-100% EtOAc-hexane) to obtain the title compound (49 mg, 52%): 1H-NMR (CD3OD; 400 MHz): δ 7.23 (d, 1H, J=2.0 Hz), 6.93 (dd, 1H, J=8.2, 2.0 Hz), 6.78 (d, 1H, J=8.2 Hz), 3.63 (m, 2H), 3.32 (m, 2H), 2.82 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained (74.3 mg)
  3. customwas dried in vacuo for 1 h
  4. dissolutiondissolved in HOAc (2 mL)
  5. temperatureThe resulting mixture was cooled to 0° C.
  6. stirringThe resulting mixture was stirred for 30 min
  7. washwashed with aq NaHCO3 (2 mL)
  8. concentrationconcentrated
  9. customThe residue was purified on silica (20-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-e9fdcac5f35948769e709caeed2c89c9
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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