2-Aminopropanol → HCID 178460298, compound

HRID 33764

Reaction equation

HRID 33764 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[S:16][N:15]=[C:14]([OH:17])[C:13]=2[C:18]#[N:19])=[CH:7][C:6]=1[F:20].[CH3:26][CH:27]([NH2:30])[CH2:28][OH:29]>C(O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[S:16][N:15]=[C:14]([OH:17])[C:13]=2[C:18]([NH:30][CH:27]([CH3:26])[CH2:28][OH:29])=[NH:19])=[CH:7][C:6]=1[F:20]

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 178510531HCID 178510531, compound

Product 1

HCID 178460298HCID 178460298, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylamino]-3-hydroxy-isothiazole-4-carbonitrile (0.2 g) and DL-2-amino-1-propanol (0.7 g) in 20 ml of ethanol was placed in a high-pressure reaction equipment and heated to 100° C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was chromatographed by silica gel column (chloroform/methanol, 25:1) to give the desired product as a light yellow solid. MS: 470; 1H NMR (DMSO-d6, 300 MHz): δ 10.60 (brs, 1/2H, NH, D2O exchangeable), 9.69 (brs, 1/2H, NH, D2O exchangeable), 9.22 (brs, 1/2H, NH, D2O exchangeable), 8.55 (s, 1H, OH, D2O exchangeable), 7.91 (brs, 1/2H, NH, D2O exchangeable), 7.70 (brs, 1/2H, NH, D2O exchangeable), 7.61 (d, 1H, J=8.7 Hz, ArH), 7.22 (dd, 1H, J=2.1, 8.7 Hz, ArH), 7.16 (t, 1H, J=8.7 Hz, ArH), 6.99 (dd, 1H, J=2.1, 12.6 Hz, ArH), 6.88 (d, 1H, J=2.1 Hz, ArH), 6.83 (dd, 1H, J=2.1, 8.7 Hz, ArH), 5.09 (brs, 1H, OH), 3.80 (m, 1H, CH), 3.49 (m, 1H, CH). 3.44 (m, 1H, CH), 1.15 (d, 3H, J=6.3 Hz, CH3).

Workup

  1. customwas placed in a high-pressure reaction equipment
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was chromatographed by silica gel column (chloroform/methanol, 25:1)

Sources & evidence

ORD record
ord-9a4cce9ebb73474b8b1e3ea58d6534f8
Source dataset
uspto-grants-2008_09
Patent number
US07429667B2

Linked notes

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