Ethanolamine → HCID 178434663, compound

HRID 407306Notes

Reaction equation

HRID 407306 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]1[S:9][C:10]2[CH:16]=[C:15]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1.C(N(CC)CC)C.[NH2:28][CH2:29][CH2:30][OH:31]>C(Cl)(Cl)Cl>[OH:31][CH2:30][CH2:29][NH:28][S:17]([C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:3]3[C:4]([CH3:7])=[N:5][NH:6][C:2]=3[NH2:1])[S:9][C:10]=2[CH:16]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 178434647HCID 178434647, compound

Product 1

HCID 178434663HCID 178434663, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The crude product (130 mg, 0.39 mmol) from the preparation of 2-(5-amino-3-methyl-1H-pyrazol-4-yl)benzothiazole-6-sulfonyl chloride was suspended in chloroform. Triethylamine (0.1 mL) and 2-aminoethanol (26 mg, 0.43 mmol) were then added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the product was purified using preparative TLC eluting with EtOAc:hexanes:MeOH=6/4/0.3 to yield 22 mg (16%) of the product as a cream coloured powder. MS (m/z, ES+): 354 (M+1, 100%); 1H NMR (400 MHz, ppm, DMSO-d6): δ 12.25-11.75 (br s, 1H, exchangeable), 8.47 (s, 1H), 7.99 (d, J=8.5 Hz, 1H), 7.81 (d, J=8.5 Hz, 1H), 7.59 (br s, 1H, SO2NH, exchangeable), 7-5.5 (br s, 2H, exchangeable), 4.66 (t, J=5.6 Hz, 1H, OH, exchangeable), 3.34 (m, J=6.2 Hz, 2H), 2.80 (br s, 2H), 2.41 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-d12c4e7cf6ce4f199d526d99790ea1ca
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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