Diisopropylethylamine → (E)-6-(3-(3-(3-Methylbenzofuran-2-yl)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 2172136노트

반응식

HRID 2172136 반응식
Cl.[CH3:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]1[CH2:15][NH:14][CH2:13]1.Cl.[O:17]=[C:18]1[NH:27][C:26]2[N:25]=[CH:24][C:23](/[CH:28]=[CH:29]/[C:30](O)=[O:31])=[CH:22][C:21]=2[CH2:20][CH2:19]1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]1[CH2:13][N:14]([C:30](=[O:31])/[CH:29]=[CH:28]/[C:23]2[CH:22]=[C:21]3[C:26](=[N:25][CH:24]=2)[NH:27][C:18](=[O:17])[CH2:19][CH2:20]3)[CH2:15]1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 67154696HCID 67154696, 화합물

생성물 1

HCID 52950833(E)-6-(3-(3-(3-Methylbenzofuran-2-yl)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one수율 58.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(3-methylbenzofuran-2-yl)azetidine hydrochloride (19.9 mg, 0.089 mmol) in DMF (2 mL) were added (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (15.8 mg, 0.062 mmol), EDCI.HCl (19.9 mg, 0.104 mmol), HOAt (14.0 mg, 0.103 mmol) and N,N-diisopropylethylamine (58 μL, 0.339 mmol). The reaction was stirred at rt for 21 h, after which the mixture was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer extracted with EtOAc. The combined organic layers were washed with brine (3×), dried with Na2SO4 and concentrated. The residue was triturated twice with Et2O and the dried to yield (the title compound (14.0 mg, 58%) as a pale orange solid.

후처리

  1. customafter which the mixture was partitioned between EtOAc and H2O
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc
  4. washThe combined organic layers were washed with brine (3×)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was triturated twice with Et2O
  8. customthe dried

출처 및 근거

ORD 기록
ord-53e3f2ec2407493d99d4639a6464ddae
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051321B2

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