Diisopropylethylamine → HCID 59353094, compound

HRID 1914721Notes

Reaction equation

HRID 1914721 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([Cl:22])=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:24][N:25]([CH2:27][C:28](Cl)=[O:29])[CH3:26].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[Cl:22][C:21]1[C:12]([NH:11][S:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:28](=[O:29])[CH2:27][N:25]([CH3:26])[CH3:24])=[CH:7][CH:6]=2)(=[O:10])=[O:9])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3302617HCID 3302617, compoundHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride2×

Product 1

HCID 59353094HCID 59353094, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-amino-N-(3-chloroquinoxalin-2-yl)benzenesulfonamide (2 g; 4.5 mmol; 1 eq) in DCM (100 mL) is added dimethylaminoacetyl chloride hydrochloride (710 mg; 4.5 mmol; 1 eq) and N-ethyldiisopropylamine (2.3 mL; 13.5 mmol; 3 eq) and the reaction mixture is stirred at room temperature overnight. To complete the reaction, dimethylaminoacetyl chloride hydrochloride (1.06 g; 6.74 mmol; 1.5 eq) is added and the reaction mixture is allowed to stir another 2 days. The precipitate formed is filtered off and the filtrate is treated with a solution of citric acid. The precipitate in the organic phase is filtered and the aqueous phase is basified with Na2CO3. The product is extracted with DCM and the organic phase is concentrated to near dryness to afford 1.5 g (80%) of the title compound as a yellow powder. HPLC (max plot) 85%; Rt 2.37 min. UPLC/MS (ES+) 420.2, (ES−) 418.3.

Workup

  1. additionis added
  2. stirringto stir another 2 days
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. additionthe filtrate is treated with a solution of citric acid
  6. filtrationThe precipitate in the organic phase is filtered
  7. extractionThe product is extracted with DCM
  8. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-561963b0d78e4018943e7b753da08aff
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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