3-Hydroxy-2,2-dimethylpropionic acid → HCID 68688264、化合物

HRID 1992159ノート

反応式

HRID 1992159 の反応式
[CH:1]([C:4]1[CH:5]=[C:6]([Mg]Br)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].C(C(=C1CCN(C(OC(C)(C)C)=O)CC1)C(OCC)=O)#N.[OH:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36](O)=[O:37].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C(C1C=C([C:84]2([CH2:90][CH2:91][N:92]3[CH:97]4[CH2:98][CH2:99][CH:93]3[CH2:94][CH:95]([N:100]3[C:104]5[CH:105]=[CH:106][CH:107]=[CH:108][C:103]=5[N:102]=[C:101]3[CH3:109])[CH2:96]4)[CH2:89][CH2:88][NH:87][CH2:86][CH2:85]2)C=CC=1)(C)C>CN(C=O)C.CCOC(C)=O>[CH:1]([C:4]1[CH:5]=[C:6]([C:84]2([CH2:90][CH2:91][N:92]3[CH:97]4[CH2:98][CH2:99][CH:93]3[CH2:94][CH:95]([N:100]3[C:104]5[CH:105]=[CH:106][CH:107]=[CH:108][C:103]=5[N:102]=[C:101]3[CH3:109])[CH2:96]4)[CH2:89][CH2:88][N:87]([C:36](=[O:37])[C:35]([CH3:40])([CH3:39])[CH2:34][OH:33])[CH2:86][CH2:85]2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

参加物

9

反応物 6

HCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11551073TERT-BUTYL 4-(1-CYANO-2-ETHOXY-2-OXOETHYLIDENE)PIPERIDINE-1-CARBOXYLATEHCID 68716332HCID 68716332、化合物HCID 178439132HCID 178439132、化合物

生成物 1

HCID 68688264HCID 68688264、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

This compound was prepared from 3-isopropyl phenylmagnesium bromide and 16a according to the procedure described in example 16. To a solution of 3-hydroxy-2,2-dimethylpropanoic acid (0.14 mmol), DIEA (1.7 mmol) and HATU (0.14 mmol) in DMF was added 1-(8-{2-[4(-3-isopropylphenyl)piperdin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole hydrochloride (0.13 mmol) in the same solvent and stirring was continued overnight. The reaction mixture was diluted with EtOAc, and washed with NaHCO3, water, and satd. brine and dried (Na2SO4). The solvent was removed in-vacuo and the crude material was purified by HPLC to 1 as a clear film. H NMR (400 MHz, CDCl3) 9.72 (s, 2H), 8.48 (s, 1H), 7.64 (d, 1H), 7.04-7.36 (m, 8H), 4.74 (t, 1H), 3.19-3.32 (m, 4H), 2.88-2.97 (m, 3H), 2.60 (s, 3H), 2.43-2.47 (d, 4H), 2.37 (s, 2H), 1.86-2.33 (m, 10H), 1.77 (d, 2H), 1.26-1.28 (d, 6H). LCMS m/z (M+H) calc: 556.79, obsd: 557.79.

後処理

  1. washwashed with NaHCO3, water
  2. dry with materialbrine and dried (Na2SO4)
  3. customThe solvent was removed in-vacuo
  4. customthe crude material was purified by HPLC to 1 as a clear film

出典と根拠

ORDレコード
ord-3dbf96bd56f64344862c437de88aaf08
出典データセット
uspto-grants-2010_01
特許番号
US07645771B2

反応ノート

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