3-Hydroxy-2,2-dimethylpropionic acid → HCID 68688264, 화합물

HRID 1992159노트

반응식

HRID 1992159 반응식
[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]

참가 물질

9

반응물 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, 화합물HCID 178439132HCID 178439132, 화합물

생성물 1

HCID 68688264HCID 68688264, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3dbf96bd56f64344862c437de88aaf08
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645771B2

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