Triethylamine → HCID 67311424, 화합물

HRID 1256131노트

반응식

HRID 1256131 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.Cl.[F:27][C:28]1([F:33])[CH2:31][CH:30]([NH2:32])[CH2:29]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([NH:32][CH:30]2[CH2:31][C:28]([F:33])([F:27])[CH2:29]2)=[O:11])[CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 225009573,3-Difluorocyclobutamine hydrochlorideHCID 53234452HCID 53234452, 화합물

생성물 1

HCID 67311424HCID 67311424, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To the mixture of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (1.09 g, 3 mmol) and 3,3-difluorocyclobutyl amine hydrochloride (1 g, 7 mmol) in DMF (10 ml), added PyBOP (1.56 g, 3 mmol) then triethyl amine (1.8 ml, 12 mmol). Stirring was kept for 3 hours. Diluted with EtOAc, washed with 1N HCl, water and brine. Dried over anhydrous sodium sulfate. Concentrated, the residue was dissolved in DMSO and purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column). The title compound was obtained as light yellow powder. MS calcd for (C19H20BF2N3O5S): 451.12. MS found (ESI negative): (M−H)−=450.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.79 (s, 1H), 9.15 (s, 1H), 8.48 (d, J=6.4 Hz, 1H), 7.43 (d, J=8.8 Hz, 1H), 7.39 (d, J=2 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.09 (dd, J=8.4 Hz, 1H), 6.40 (d, J=2 Hz, 1H), 6.35 (dd, J=8.4 Hz, 1H), 5.92 (s, 2H), 4.85 (s, 2H), 4.05 (m, 1H), 3.75 (s, 2H), 2.89 (m, 2H), 2.59 (m, 2H).

후처리

  1. washwashed with 1N HCl, water and brine
  2. dry with materialDried over anhydrous sodium sulfate
  3. concentrationConcentrated
  4. dissolutionthe residue was dissolved in DMSO
  5. custompurified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

출처 및 근거

ORD 기록
ord-295fea5890a5483993563d95a6780fff
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461134B2

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