Diisopropylethylamine → (S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1972050노트

반응식

HRID 1972050 반응식
[CH2:1]([C:5]1[N:10]=[N:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:51]([O:55][C:56]([N:58]1[CH2:62][C@H:61]([CH2:63][NH2:64])[O:60][C:59]1([CH3:66])[CH3:65])=[O:57])([CH3:54])([CH3:53])[CH3:52].CCN(C(C)C)C(C)C>CN(C=O)C.CCOCC.O>[C:51]([O:55][C:56]([N:58]1[CH2:62][C@H:61]([CH2:63][NH:64][C:11]([C:8]2[N:9]=[N:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:6]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:18][CH:19]=3)[CH:7]=2)=[O:13])[O:60][C:59]1([CH3:66])[CH3:65])=[O:57])([CH3:54])([CH3:53])[CH3:52]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673720716-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acidHCID 67373621(S)-5-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67373730(S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (Example 93, 0.34 mmol, 0.12 g), HBTU (0.34 mmol, 0.13 g) and (S)-5-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.34 mmol, 0.05 mL) in DMF was added DIEA (1.0 mmol, 0.17 mL). Upon completion of the reaction, the mixture was diluted with ether, and then poured into water. The resulting mixture was extracted, the organic layer was dried. The solvent was removed, and the resulting residue was chromatographed with 4:1 hexane/EtOAc to provide (S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester was used as is in the next step. LCMS: m/z 566.9 [M+1].

후처리

  1. customUpon completion of the reaction
  2. extractionThe resulting mixture was extracted
  3. customthe organic layer was dried
  4. customThe solvent was removed
  5. customthe resulting residue was chromatographed with 4:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-efb4df4473d544a29b88060d1495a861
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431575B2

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