Ethanolamine → HCID 58367154, compound

HRID 1891491Notes

Reaction equation

HRID 1891491 reaction equation
O[CH:2]1[C:10]2[C:5](=[C:6]([C:11]3[S:15][C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH:23]=4)[C:21]#[N:22])=[N:13][CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.C([N:35]([CH:38]([CH3:40])C)[CH2:36]C)(C)C.C(CN)[OH:42]>C(Cl)Cl>[OH:42][CH:40]1[CH2:36][N:35]([CH:2]2[C:10]3[C:5](=[C:6]([C:11]4[S:15][C:14]([C:16]5[CH:17]=[CH:18][C:19]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH:23]=5)[C:21]#[N:22])=[N:13][CH:12]=4)[CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)[CH2:38]1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 53232427HCID 53232427, compound

Product 1

HCID 58367154HCID 58367154, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 20: To a stirred solution of 5-(5-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile (20 mg, 0.05 mmol) in DCM (1 mL) was added thionyl chloride (12.6 mg, 0.106 mmol) at 0° C. The reaction was stirred at room temperature for 3 h. The solvent was evaporated and the crude chloride re-dissolved in dimethyl acetamide (1 mL). Diisopropyl ethylamine (20.5 mg, 0.16 mmol) and ethanolamine (9.7 mg, 0.16 mmol) were added and the reaction mixture was stirred at 70° C. overnight. The reaction mixture was quenched with water (200 uL) and purified by preparative HPLC to afford 11 mg (46%) of 5-(5-(1-(3-hydroxyazetidin-1-yl)-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile 208. LCMS-ESI (m/z) calculated for C25H25N3O2S: 431.1; found 432.1 [M+H]+, tR=6.48 min (Method 2).

Workup

  1. customPrepared
  2. customThe solvent was evaporated
  3. dissolutionthe crude chloride re-dissolved in dimethyl acetamide (1 mL)
  4. stirringthe reaction mixture was stirred at 70° C. overnight
  5. customThe reaction mixture was quenched with water (200 uL)
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-89fe914de7c24217b5085b1210d89617
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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