Triethylamine → methyl 3-(4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)propanoate

HRID 1429559Notes

Reaction equation

HRID 1429559 reaction equation
[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1.C(N(CC)CC)C.Cl[S:37]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])(=[O:39])=[O:38]>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][N:26]([S:37]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])(=[O:39])=[O:38])[CH2:27][CH:28]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4962888Methyl 3-(chlorosulfonyl)propanoateHCID 674670502-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

Product 1

HCID 67468148methyl 3-(4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)propanoateYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (95 mg, 0.230 mmol) and triethylamine (0.065 mL, 0.459 mmol) in CH2Cl2 (2 mL) at 0° C. was added methyl 3-(chlorosulfonyl)propanoate (64 mg, 0.345 mmol). The reaction mixture was stirred at this temperature for 15 min, then at rt for 2 h. The reaction mixture was quenched with sat. aq. NaHCO3 (2 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 70% EtOAc) to afford methyl 3-(4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)propanoate (80 mg, 0.142 mmol, 62% yield) as a yellow solid. LCMS (m/z)=564 (M+H)+.

Workup

  1. waitat rt for 2 h
  2. customThe reaction mixture was quenched with sat. aq. NaHCO3 (2 mL)
  3. extractionextracted with CH2Cl2 (3×5 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 70% EtOAc)

Sources & evidence

ORD record
ord-696a3c4e2c8e46c586ce2f11ae47d760
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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