Triethylamine → HCID 21048957, compound

HRID 2212390Notes

Reaction equation

HRID 2212390 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.[CH3:37][N:38]([CH3:43])[S:39](Cl)(=[O:41])=[O:40].C([N:46](CC)CC)C.CC(N(C)C)=O>ClCCl.C(OCC)(=O)C>[CH3:37][N:38]([CH3:43])[S:39](=[O:41])(=[O:40])[NH:46][CH:14]1[CH2:15][CH2:16][C:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 83372Dimethylsulphamoyl chlorideHCID 69583707HCID 69583707, compound

Product 1

HCID 21048957HCID 21048957, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Intermediate R (102 mg, 0.26 mmol) in dichloromethane (3 ml) was treated with N,N dimethylsulfamoyl chloride (112 μL, 0.80 mmol) followed by triethylamine (74 μl, 0.52 mmol) and dimethylacetamide (1 ml). After 2 hours stirring at room temperature the reaction was diluted with ethyl acetate and washed with H2O and brine, dried (MgSO4) and evaporated to an oil which crystallised on standing. 1H NM (360 MHz, CDCl3) δ 7.39–7.31 (4H, m), 7.09–7.04 (2H, m), 6.89–6.87 (1H, m), 4.56–4.54 (1H, d, J=7.2 Hz), 3.55–3.49 (1H, m), 2.82 (6H, s), 2.61–2.35 (4H, m), 2.06–1.97 (2H, m), 1.57–1.44 (2H, m). m/z=491, 493 [MH]−

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated to an oil which
  4. customcrystallised

Sources & evidence

ORD record
ord-e606448d0e214f13beabb98019f15bcc
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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