1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-hydroxy-adamantane-1-carboxylic acid (5,6-dihydro-4H-cyclopentathiazol-2-yl)-amide

HRID 1470044노트

반응식

HRID 1470044 반응식
Cl.[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH2:10].[OH:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([C:22](O)=[O:23])([CH2:15]3)[CH2:13]1)[CH2:19]2.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[S:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[N:4]=[C:3]1[NH:10][C:22]([C:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][C:12]([OH:11])([CH2:21]3)[CH2:13]1)[CH2:20]2)=[O:23]

참가 물질

7

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365183-Hydroxyadamantane-1-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 162532465,6-Dihydro-4H-cyclopenta[d]thiazol-2-amine hydrochloride

생성물 1

HCID 871864543-hydroxy-adamantane-1-carboxylic acid (5,6-dihydro-4H-cyclopentathiazol-2-yl)-amide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A mixture of Example 209A (921 mg, 5.19 mmol), 3-hydroxy-adamantane-1-carboxylic acid (1.22 g, 6.2 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (2.0 g, 10.4 mmol), 1-hydroxybenzotriazole hydrate (846 mg, 10.4 mmol) and 4-dimethylaminopyridine (196 mg, 1.04 mmol) in pyridine (20 mL) was stirred at room temperature for 12 hours. The solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, 50% ethyl acetate/hexanes) afforded the title compound. MS (ESI) m/z 319 (M+H)+.

후처리

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel, 50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8ed247fa01d44a269291973c15e35436
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006275B2

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