Triethylamine → 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-[1,3,4]-thiadiazol-2-yl)-urea

HRID 1182137

Reaction equation

HRID 1182137 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:6][CH2:7][N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9]1)[CH2:4][OH:5].C1([O:26][C:27](=O)[NH:28][C:29]2[S:30][C:31]([CH2:34][CH3:35])=[N:32][N:33]=2)C=CC=CC=1.C(N(CC)CC)C>CS(C)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH:10]2[CH2:11][N:8]([CH2:7][CH2:6][C@H:3]([NH:2][C:27]([NH:28][C:29]3[S:30][C:31]([CH2:34][CH3:35])=[N:32][N:33]=3)=[O:26])[CH2:4][OH:5])[CH2:9]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66876196Phenyl 5-ethyl-1,3,4-thiadiazol-2-ylcarbamateHCID 69410461(S)-2-amino-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-butan-1-ol hydrochloride

Product 1

HCID 102380831-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-[1,3,4]-thiadiazol-2-yl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (S)-2-amino-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-butan-1-ol hydrochloride (1.04 g, 2.82 mmol), (5-Ethyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester (0.70 g, 2.82 mmol) and triethylamine (1.6 ml, 11.28 mmol) in DMSO (70 ml) is stirred at ambient temperature for 18 hour, then partitioned between ethylacetate and saturated aqueous sodium bicarbonate solution. The organic phase is washed with brine, dried over MgSO4 and evaporated. The crude product is purified by recrystallisation from hot ethylacetate to afford 1-{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(5-ethyl-[1,3,4]-thiadiazol-2-yl)-urea. [M+H] 426.18.

Workup

  1. custompartitioned between ethylacetate and saturated aqueous sodium bicarbonate solution
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by recrystallisation from hot ethylacetate

Sources & evidence

ORD record
ord-3defff3aceb94497ac3664ec2917495e
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Linked notes

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