Diisopropylethylamine → 2-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide

HRID 60558노트

반응식

HRID 60558 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[CH2:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:47][C:48]1[CH:49]=[CH:50][C:51]2[C:55]([CH3:57])([CH3:56])[O:54][B:53]([OH:58])[C:52]=2[CH:59]=1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[CH2:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:47][C:48]1[CH:49]=[CH:50][C:51]2[C:55]([CH3:56])([CH3:57])[O:54][B:53]([OH:58])[C:52]=2[CH:59]=1)=[O:6]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58373146HCID 58373146, 화합물HCID 669277036-amino-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

생성물 1

HCID 669274352-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-chloro-4-vinyl benzoic acid (44 mg, 0.24 mmol) in DMF (2 mL) was added HATU (55 mg, 0.15 mmol) and DIEA (25 mg, 0.21 mmol). After 1 hour 6-amino-3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol hydrochloride salt (30 mg, 0.14 mmol) was added. After 12 hours the reaction was concentrated down under reduced pressure onto celite. The crude material was subjected to flash chromatography (Isco Companion, 4 g SiO2 cartridge, SiO2 solid load, neat DCM to 10% MeOH gradient) to give 2-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide as a white powder. Amount obtained: 20.8 mg (48%). Data: LCMS (M/Z): 342 (M+H); 1H NMR (DMSO-d6) δ: 1.36-1.59 (m, 6 H) 5.42 (d, J=11.1 Hz, 1 H) 6.02 (d, J=17.8 Hz, 1 H) 6.79 (dd, J=17.7, 11.0 Hz, 1 H) 7.33-7.46 (m, 1 H) 7.56 (s, 2 H) 7.69 (d, J=1.6 Hz, 2 H) 8.05 (dd, J=1.7, 0.5 Hz, 1 H) 9.00 (br. s, 1 H) 10.35-10.62 (m, 1 H).

후처리

  1. concentrationAfter 12 hours the reaction was concentrated down under reduced pressure onto celite

출처 및 근거

ORD 기록
ord-bdc28bb7c78b43e68c7b40bf777bbe32
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440994B2

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