Triethylamine → HCID 22000432, compound

HRID 1976123Notes

Reaction equation

HRID 1976123 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[N:11][C:10]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:32]([CH3:31])(=[O:34])=[O:33])=[N:11][C:10]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22000426HCID 22000426, compound

Product 1

HCID 22000432HCID 22000432, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-(9-fluoro-5,6-dihydro-4H-benzo[6,7]cyclohepta[d][1,3]thiazol-2-yl)-5-aminopentanamide (115 mg, 0.34 mmole) was dissolved in 2 ml of dry THF, cooled with an ice bath, triethylamine was added (96 μl, 0.69 mmole) followed by addition of 27 μl of methane sulfonyl chloride (0.35 mmole). The reaction mixture was stirred at room temperature for 6 hours, quenched with saturated sodium carbonate solution and extracted with 3×3 ml of ethyl acetate. The combined ethyl acetate extracts were washed with saturated sodium chloride solution, concentrated and chromatographed (12 g of silica gel, EtOAc/hexanes/7N NH3 in MeOH, 50:50:2) to give 53 mg of the desired product as a white solid (38%): m.p. 145-147° C.; 412 (ESMS, MH+).

Workup

  1. temperaturecooled with an ice bath
  2. customquenched with saturated sodium carbonate solution
  3. extractionextracted with 3×3 ml of ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with saturated sodium chloride solution
  5. concentrationconcentrated
  6. customchromatographed (12 g of silica gel, EtOAc/hexanes/7N NH3 in MeOH, 50:50:2)

Sources & evidence

ORD record
ord-528b6539e9154fcfa851dd07a2e8cc78
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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