Cyclohexylamine → 2-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-cyclohexylacetamide

HRID 1256126ノート

反応式

HRID 1256126 の反応式
[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.[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]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:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:11])[CH:7]=1

参加物

7

反応物 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 53234452HCID 53234452、化合物

生成物 1

HCID 673125302-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-cyclohexylacetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 cyclohexyl amine (1.4 ml, 12 mmol) in DMF (10 ml), added PyBOP (1.56 g, 3 mmol) then triethyl amine (0.4 ml, 3 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 (C21H26BN3O5S): 443.17. MS found (ESI negative): (M−H)−=442.2. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.87 (s, 1H), 7.90 (d, J=6 Hz, 1H), 7.41 (s, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.20 (d, J=8 Hz, 1H), 7.08 (dd, J=8 Hz, 1H), 6.45 (d, J=2 Hz, 1H), 6.33 (dd, J=8.8 Hz, 1H), 4.85 (s, 2H), 3.75 (s, 2H), 3.55 (m, 1H), 1.80-1.50 (m, 5H), 1.30-1.10 (m, 5H).

後処理

  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)

出典と根拠

ORDレコード
ord-62ea8b2b3eb645389ef774365e642126
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

反応ノート

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