3-Iodobenzoic acid → 3-iodo-N-(1-(pyridin-2-yl)cyclopropyl)benzamide

HRID 2068414

반응식

HRID 2068414 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1([NH2:20])[CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:20][C:17]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH2:19][CH2:18]1)=[O:7]

참가 물질

8

반응물 5

HCID 120603-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111054091-(Pyridin-2-yl)cyclopropanamine

생성물 1

HCID 672176523-iodo-N-(1-(pyridin-2-yl)cyclopropyl)benzamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

3-Iodobenzoic acid (2.7 g, 11.1 mmol, 1 eq), 1-(pyridin-2-yl)cyclopropanamine (1.5 g, 11.1 mmol, 1 eq), EDCI.HCl (3.2 g, 16.7 mmol, 1.5 eq), HOBT (2.2 g, 16.7 mmol, 1.5 eq) and DIPEA (6 ml, 33.5 mmol, 3 eq) were dissolved in DCM and the resulting mixture was stirred at room temperature for 18 hours. Water was added to the mixture and the product was extracted with DCM. The organic layer was concentrated and the product crystallized using dichloromethane and hexane. Yield: 2.3 g (57%). 1HNMR (400 MHz, DMSO-d6): δ 1.26 (m, 2H), 1.54 (m, 2H), 7.13 (t, J=4.04 Hz, 1H), 7.29 (m, 2H), 7.69 (t, J=8.06 Hz, 1H), 7.92 (d, J=3.05 Hz, 2H), 8.29 (s, 1H), 8.45 (d, J=4.56 Hz, 1H), 9.33 (s, 1H).

후처리

  1. extractionthe product was extracted with DCM
  2. concentrationThe organic layer was concentrated
  3. customthe product crystallized

출처 및 근거

ORD 기록
ord-39e2177816c843dab1eaae166f78e304
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293909B2

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