1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Edoxaban

HRID 1986040노트

반응식

HRID 1986040 반응식
[NH2:1][C@@H:2]1[CH2:7][C@@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:5][CH2:4][C@@H:3]1[NH:13][C:14](=[O:25])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)=[O:16].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:38][N:39]1[CH2:44][CH2:43][C:42]2[N:45]=[C:46]([C:48](O)=[O:49])[S:47][C:41]=2[CH2:40]1.Cl.CN(C)CCCN=C=NCC>CC(N(C)C)=O.O.C(N(CC)CC)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C:14]([NH:13][C@H:3]2[CH2:4][CH2:5][C@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:7][C@H:2]2[NH:1][C:48]([C:46]2[S:47][C:41]3[CH2:40][N:39]([CH3:38])[CH2:44][CH2:43][C:42]=3[N:45]=2)=[O:49])=[O:25])=[N:19][CH:20]=1

참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 111490315-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid--hydrogen chloride (1/1)HCID 59676986EthanediaMide iMpurity F

생성물 1

HCID 10280735Edoxaban수율 81.8%

시약·촉매·용매 3

HCID 962Water용매HCID 8471Triethylamine용매HCID 31374Dimethylacetamide용매

실험 절차

N1-{(1S,2R,4S)-2-Amino-4-[(dimethylamino)carbonyl]cyclohexyl}-N2-(5-chloropyridin-2-yl)ethanediamide (553.4 mg) was dissolved in dimethylacetamide (7 mL), and to the solution were added 1-hydroxybenzotriazole monohydrate (245.1 mg), 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride (386.0 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (345.0 mg) at room temperature. The resultant mixture was stirred for 13 hours, and triethylamine and water were added thereto. The precipitated crystals were collected by filtration, and were dried, to thereby give 674.1 mg of the title compound.

후처리

  1. filtrationThe precipitated crystals were collected by filtration
  2. customwere dried

출처 및 근거

ORD 기록
ord-915072779a4c4453842ae556f81ef9eb
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547786B2

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