Sulfamide → HCID 21963966, compound

HRID 2212389Notes

Reaction equation

HRID 2212389 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[F:36])[CH2:16][CH2:15][CH:14](CS(N3CCC[C@@H]3C(O)=O)(=O)=O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:37]([NH2:41])([NH2:40])(=[O:39])=[O:38]>O1CCOCC1.C(OCC)(=O)C.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[F:36])[CH2:16][CH2:15][CH:14]([NH:40][S:37](=[O:39])(=[O:38])[NH2:41])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 82267SulfamideHCID 69583707HCID 69583707, compound

Product 1

HCID 21963966HCID 21963966, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Intermediate R (100 mg, 0.26 mmol in dioxane (4 ml) was treated with sulfamide (125 mg, 1.30 mmol) and heated to reflux for 1 hour, then cooled to room temperature, diluted with ethyl acetate, washed with H2O, dried (MgSO4) and evaporated. Trituration of the residue in ether afforded the desired product (50 mg, 42% yield). 1H NMR (360 MHz, CDCl3) δ 7.40–7.30 (4H, m), 7.09–7.02 (2H, m), 6.90–6.80 (1H, m), 5.51–5.46 (1H, m), 5.14–5.07 (2H, broad, s) 3.70–3.61 (1H, m), 2.60–2.49 (3H, m), 2.19–2.10 (2H, m) and 1.99–1.45 (3H, m). m/z=465, 467 [MH]+

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-14310fcb39d449258ec2bf4031f4a785
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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