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

반응식

HRID 1182137 반응식
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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3defff3aceb94497ac3664ec2917495e
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288537B2

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