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Phenyl chloroformate → (4-{[Methyl-(3-methyl-pyrazine-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid phenyl ester

HRID 1685028
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HRID 1685028 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]([CH3:18])[C:9]([C:11]2[C:16]([CH3:17])=[N:15][CH:14]=[CH:13][N:12]=2)=[O:10])[N:6]=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C1COCC1>[C:23]1([O:22][C:20](=[O:21])[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][N:8]([CH3:18])[C:9]([C:11]3[C:16]([CH3:17])=[N:15][CH:14]=[CH:13][N:12]=3)=[O:10])[N:6]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
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참가 물질

6

반응물 2

HCID 15891Phenyl chloroformateHCID 86661291N-((2-aminothiazol-4-yl)methyl)-N,3-dimethylpyrazine-2-carboxamide

생성물 1

HCID 58055095(4-{[Methyl-(3-methyl-pyrazine-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid phenyl ester수율 17.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A mixture of N-((2-aminothiazol-4-yl)methyl)-N,3-dimethylpyrazine-2-carboxamide (555 mg, 1.84 mmol) and DMAP (20 mg) in pyridine (10 mL) was cooled to 0° C. and a solution of phenyl chloroformate (433 mg, 2.8 mmol) in THF was added drop wise. The mixture was stirred overnight and all volatiles were removed in vacuo at 30° C. The residue was triturated with TBME to afford (4-{[Methyl-(3-methyl-pyrazine-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid phenyl ester (125 mg) as a tan colored solid (purity 96%).

후처리

  1. customall volatiles were removed in vacuo at 30° C
  2. customThe residue was triturated with TBME

출처 및 근거

ORD 기록
ord-1c18361e42ab450686be6dd049c8ff95
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08148380B2

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