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

HRID 60558

反応式

HRID 60558 の反応式
[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]

参加物

6

反応物 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、化合物HCID 669277036-aMino-3,3-diMethylbenzo[c][1,2]oxaborol-1(3H)-ol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-bdc28bb7c78b43e68c7b40bf777bbe32
出典データセット
uspto-grants-2016_09
特許番号
US09440994B2

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