1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-{(1E)-3-[4-(2-Hydroxyethyl)piperidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 2171967

반응식

HRID 2171967 반응식
Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:37]1[CH2:42][CH2:41][CH:40]([CH2:43][CH2:44][OH:45])[CH2:39][CH2:38]1.CCN=C=NCCCN(C)C>CN(C=O)C>[OH:45][CH2:44][CH2:43][CH:40]1[CH2:41][CH2:42][N:37]([C:15](=[O:17])/[CH:14]=[CH:13]/[C:8]2[CH:7]=[C:6]3[C:11](=[N:10][CH:9]=2)[NH:12][C:3](=[O:2])[CH2:4][CH2:5]3)[CH2:38][CH2:39]1

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 739534-PiperidineethanolHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

생성물 1

HCID 529504366-{(1E)-3-[4-(2-Hydroxyethyl)piperidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (50 mg, 0.20 mmol), DMF (4.8 mL), HOBt (32 mg, 0.23 mmol), DIPEA (78 μL, 0.47 mmol), 4-piperidineethanol (30 mg, 0.23 mmol) and EDAC (45 mg, 0.23 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified on column chromatography (eluent: dichloromethane/MeOH, 95/5) to give a white solid. This solid was triturated in MeOH, filtered, washed with MeOH and diethyl ether and dried to give the title compound (35 mg, 55%) as a white solid.

후처리

  1. concentrationconcentrated to dryness
  2. customThe residue was purified on column chromatography (eluent: dichloromethane/MeOH, 95/5)
  3. customto give a white solid
  4. customThis solid was triturated in MeOH
  5. filtrationfiltered
  6. washwashed with MeOH and diethyl ether
  7. customdried

출처 및 근거

ORD 기록
ord-710e6b5cff6d4176beb7cc77556c9185
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051321B2

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