3-Methylbenzoic acid → Dimethyl 5,5'-(N-{[6-amino-5-({3-[(3-methylbenzoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}sulfonimidoyl)dipentanoate

HRID 1042938노트

반응식

HRID 1042938 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1[C:29]#[C:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=1.[C:38]1([CH3:47])[CH:43]=[CH:42][CH:41]=[C:40]([C:44](O)=[O:45])[CH:39]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1[C:29]#[C:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:44](=[O:45])[C:40]2[CH:41]=[CH:42][CH:43]=[C:38]([CH3:47])[CH:39]=2)[CH:32]=1

참가 물질

7

반응물 4

HCID 74183-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86668543Dimethyl 5,5'-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

생성물 1

HCID 71525724Dimethyl 5,5'-(N-{[6-amino-5-({3-[(3-methylbenzoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}sulfonimidoyl)dipentanoate수율 78.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To the reaction solution of dimethyl 5,5′-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate (80 mg, 0.15 mmol, 1.0 equiv.), m-toluic acid (60 mg, 0.2 mmol, 1.3 equiv.), and DIPEA (0.11 mL, 0.6 mmol, 4.0 equiv.) in anhydrous DMF (1 mL) was added BOP (120 mg, 0.27 mmol, 1.8 equiv.) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for overnight. It was then diluted with EtOAc, washed with sat. aq. NaHCO3, aq. NH4Cl, and brine, and finally dried with anhydrous Na2SO4. The solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:3 to 4:1) to afford the title compound as clear oil (76 mg). 1H NMR (DMSO-d6) δ: 10.29 (s, 1H), 8.57 (d, J=2.1 Hz, 1H), 8.07 (t, J=1.8 Hz, 1H), 8.04 (d, J=2.3 Hz, 1H), 7.79 (s, 1H), 7.74-7.78 (m, 2H), 7.38-7.46 (m, 4H), 7.00 (br. s., 2H), 3.54-3.63 (m, 10H), 2.41 (s, 3H), 2.39 (t, J=7.3 Hz, 4H), 1.71-1.86 (m, 4H), 1.64-1.71 (m, 4H)

후처리

  1. washwashed with sat. aq. NaHCO3, aq. NH4Cl, and brine
  2. dry with materialfinally dried with anhydrous Na2SO4
  3. customThe solution was decanted
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0834c607834c4297be70d805e8287c24
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08558002B2

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