Ethanolamine → HCID 11993494, compound

HRID 1364491Notes

Reaction equation

HRID 1364491 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH2:20]([CH2:22][NH2:23])[OH:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:21][CH2:20][CH2:22][NH:23][S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11993494HCID 11993494, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step 1 of Example 9 (110 mg; 0.33 mmol; 1 eq.), is dissolved in DCM (10 ml). Ethanolamine (39.9 mg; 0.65 mmol; 2 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After one hour, the solvents are evaporated. The crude product is dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, Compound (11) is obtained as white-off solid (36.5 mg; 30%). 1H NMR (DMSO-d6) δ 2.15 (s, 3H), 2.43 (s, 3H), 2.91 (m, 2H), 3.41 (m, 2H), 4.72 (t, J=6 Hz, 1H), 7.21 (d, J=4.5 Hz, 1H), 7.54 (d, J=4.5 Hz, 1H), 7.88 (br s, 1H), 12.25 (br s, 1H). M−(ESI): 360.11; M+(ESI): 362.06. HPLC, Rt: 2.36 min (purity: 97.5%).

Workup

  1. customthe solvents are evaporated
  2. dissolutionThe crude product is dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-3988aa0f71ea45eb80effb12f1a113e2
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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