1-Hydroxybenzotriazole → 2,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide

HRID 2080186노트

반응식

HRID 2080186 반응식
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:34]([C:41]1[S:45][C:44]([CH2:46][NH2:47])=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:47][CH2:46][C:44]1[S:45][C:41]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:42][CH:43]=1)=[O:6]

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189772452,6-Diaminonicotinic acidHCID 231306122-Thiophenemethanamine,5-(phenylmethyl)-

생성물 1

HCID 231303582,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide수율 30%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 2,6-diaminonicotinic acid described in Preparation Example A-15 (173 mg, 1.13 mmol) in dimethylsulfoxide (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (433 mg, 2.26 mmol), 1-hydroxybenzotriazole (346 mg, 2.26 mmol) and C-(5-benzyl-thiophen-2-yl)-methylamine described in Preparation Example 42 (230 mg, 1.13 mmol), and the solution was stirred at room temperature fro 16 hours 30 minutes. The reaction solution was poured into brine, the solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to NH silica gel column chromatography, eluted with solvent (ethyl acetate) and the title compound (114 mg, 0.34 mmol, 30%) was obtained.

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with solvent (ethyl acetate)

출처 및 근거

ORD 기록
ord-66fafe050d8140739905096af590ecdc
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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