Benzenesulfonyl chloride → HCID 136263766, compound

HRID 880016Notes

Reaction equation

HRID 880016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=3)[NH:16][CH:15]=2)=[N:12][N:13]=1.[CH2:29]([N:31](CC)CC)[CH3:30].CN(C1C=CC=CN=1)C.C1(S(Cl)(=O)=O)C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:30][C:29]#[N:31])[C:9]1[O:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=3)[NH:16][CH:15]=2)=[N:12][N:13]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 136263772HCID 136263772, compound

Product 1

HCID 136263766HCID 136263766, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 g of (2-chlorophenyl)-{5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]-pyridin-3-yl]-1,3,4-oxadiazol-2-yl}amine are dissolved in 15 ml of DMF at 60° C. When the solution has re-cooled to RT, 1.4 ml of triethylamine and 40 mg of dimethylaminopyridine are added. This solution is then cooled to 0° C., before 0.5 ml of benzenesulfonyl chloride is added dropwise. When the addition is complete, the batch is stirred at RT for a further 4 h. After undissolved constituents have been filtered off, the solution which remains is evaporated completely to dryness, and the residue is partitioned between ethyl acetate and water, with crystals precipitating out after a short time. The product is filtered off with suction and combined with the second crystal batch, giving 1.3 g of the title compound. HPLC-MS: Rt=2.567 min; [M+H+]: 532.1

Workup

  1. additionis added dropwise
  2. additionWhen the addition
  3. filtrationAfter undissolved constituents have been filtered off
  4. customthe solution which remains is evaporated completely to dryness
  5. customthe residue is partitioned between ethyl acetate and water, with crystals
  6. customprecipitating out after a short time
  7. filtrationThe product is filtered off with suction

Sources & evidence

ORD record
ord-4f2c937187714ea7adcce2b91c9e110f
Source dataset
uspto-grants-2015_03
Patent number
US08993564B2

Reaction notes

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