Triethylamine → HCID 90954427, compound

HRID 346494Notes

Reaction equation

HRID 346494 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[S:7][N:6]=1)[CH3:4].C(N(CC)CC)C.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28]>C(Cl)Cl>[C:25]([NH:1][CH2:2][CH:3]([C:5]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[S:7][N:6]=1)[CH3:4])(=[O:29])[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 86611452HCID 86611452, compound

Product 1

HCID 90954427HCID 90954427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [3-(2-amino-1-methylethyl)-1,2,4-thiadiazol-5-yl]carbamate (0.27 mmol) was dissolved in DCM (5 mL) and triethylamine (1.4 eq) was added followed by n-butyric acid chloride (1.1 eq). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. Purification, using preparative LCMS (30–70% MeCN over 10 min followed by 100% MeCN for 5 min), afforded tert-butyl [3-(2-butyrylamino-1-methyl-ethyl)-[1,2,4]thiadiazol-5-yl]-carbamate. Deprotection was carried out in DCM (1 mL) and TFA (1 mL) was added. The reaction mixture was stirred for 1.5 h at room temperature. The solvent was removed under reduced pressure affording the crude product which was converted to the sulfonamide using method C without any further purifications.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification
  3. customLCMS (30–70% MeCN over 10 min followed by 100% MeCN for 5 min)

Sources & evidence

ORD record
ord-ba3fef29db844c86b705bf52e919a9ed
Source dataset
uspto-grants-2007_02
Patent number
US07173030B2

Reaction notes

Loading…