Triethylamine → HCID 54756257, compound

HRID 530973Notes

Reaction equation

HRID 530973 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C(N(CC)CC)C.Cl[CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:33]([CH:32]=[CH2:31])(=[O:35])=[O:34])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 19963206HCID 19963206, compound

Product 1

HCID 54756257HCID 54756257, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dichloromethane (10 mL), compound 41 (100 mg, 0.337 mmol) and triethylamine (141 μL, 1.02 mmol) was cooled to 0° C. 2-chloro-1-ethane sulfonyl chloride (32 μL, 0.304 mmol) was added and the reaction was allowed to proceed for 1 hour prior to removal of a precipitate and addition of saturated sodium bicarbonate (10 mL) and extraction with dichloromethane (2×10 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (24 mg, 20% yield): 1H NMR (400 MHz, DMSO) δ 10.81 (br, 1H), 10.13 (s, 1H), 8.75 (s, 1H), 8.02 (s, 1H), 7.58 (d, J=8.9, 2H), 7.25 (m, 3H), 6.83 (dd, J=16.4, 10.0, 1H), 6.15 (d, J=16.5, 1H), 6.07 (d, J=10.0, 1H), 3.99 (s, 3H), 3.98 (s, 3H); 13C NMR (100 MHz, DMSO) δ 157.93, 156.16, 150.10, 149.26, 136.23, 135.75, 132.76, 127.82, 125.54, 120.00, 107.16, 103.16, 100.51, 56.55, 56.45; [M+H]+ calculated for C18H18N4O4S 387.1, found 387.4.

Workup

  1. customto removal of a precipitate and addition of saturated sodium bicarbonate (10 mL) and extraction with dichloromethane (2×10 mL)
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-894f113cdf5842a993a09dcef6914146
Source dataset
uspto-grants-2016_05
Patent number
US09353116B2

Reaction notes

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