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2-Amino-6-fluorobenzylamine → [1,6]Naphthyridine-2-carboxylic acid (trans-2-phenyl-cyclopropyl)-amide

HRID 1383414
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HRID 1383414 반응식
N[C:2]1[CH:21]=[CH:20][CH:19]=[C:18](F)[C:3]=1[CH2:4][NH:5][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[N:13][CH:14]=2)[N:9]=1)=[O:7].N1C2C(=CN=CC=2)C=[CH:25][C:24]=1C(O)=O.O.ON1C2C=CC=CC=2N=N1.NC1C=CC=C(F)C=1CN>CN(C=O)C>[C:19]1([C@@H:18]2[CH2:3][C@H:4]2[NH:5][C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[N:13][CH:14]=3)[N:9]=2)=[O:7])[CH:20]=[CH:21][CH:2]=[CH:25][CH:24]=1
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참가 물질

6

반응물 4

HCID 5789982-Amino-6-fluorobenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 18621328N-(2-amino-6-fluorobenzyl)-2-[1,6]naphthyridinecarboxamide

생성물 1

HCID 57280006[1,6]Naphthyridine-2-carboxylic acid (trans-2-phenyl-cyclopropyl)-amide수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound #16 N-(2-amino-6-fluorobenzyl)-2-[1,6]naphthyridinecarboxamide To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (1.0 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 2-amino-6-fluorobenzylamine (60.0 μL) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum. Flash column chromatography of the residue (50% hexane/ethyl acetate to 100% ethyl acetate) afforded the desired product as a white solid (80.0 mg, 94%): m.p. 165 (dec.).

후처리

  1. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-a2ff9ea586d846c2b30b8a6db54029d2
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06255318B1

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