4-Methylmorpholine → HCID 178523397, 화합물

HRID 1396946노트

반응식

HRID 1396946 반응식
[CH:1]1([CH2:6][C@H:7]([CH2:18][N:19]([CH:28]=[O:29])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]([N:10]2[C@H:14]([C:15](O)=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[N+:54]1([O-:61])[C:55]([NH2:60])=[CH:56][CH:57]=[CH:58][CH:59]=1>C(#N)C>[CH:1]1([CH2:6][C@H:7]([CH2:18][N:19]([CH:28]=[O:29])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:60][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][N+:54]=3[O-:61])=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 27340604-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-iumHCID 86706370(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acidHCID 178507601HCID 178507601, 화합물

생성물 1

HCID 178523397HCID 178523397, 화합물수율 62%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (88 mg, 0.219 mmol) in acetonitrile (4 mL) at 0° C. was added 4-methylmorpholine (0.053 mL, 0.482 mmol), followed by 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium (DMTMM) (86 mg, 0.263 mmol). The solution was stirred for 15 min, and then 2-pyridinamine 1-oxide (31.4 mg, 0.285 mmol) was added. The reaction mixture was warmed up to room temperature and stirred overnight. The solvent was evaporated away, and residue was dissolved in DCM. The solution was washed with 5% aq. NaHSO4 followed by water. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford a crude oil, which was purified by RP-HPLC to provide (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide as a colorless gum (67 mg, 62%). LCMS: (M+H)+: 494.0.

후처리

  1. stirringstirred overnight
  2. customThe solvent was evaporated away
  3. dissolutionresidue was dissolved in DCM
  4. washThe solution was washed with 5% aq. NaHSO4
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude oil, which
  9. customwas purified by RP-HPLC

출처 및 근거

ORD 기록
ord-cc7a9ed7d8fb4cc79a6a7909bf33d316
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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