1-Methylimidazole → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

HRID 1396936노트

반응식

HRID 1396936 반응식
CN1C=CN=C1.[CH:7]1([CH2:12][C@H:13]([CH2:24][N:25]([CH:34]=[O:35])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]([N:16]2[C@H:20]([C:21]([OH:23])=O)[CH2:19][CH:18]=[N:17]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1.S(Cl)(C)(=O)=O.[F:41][C:42]1[CH:43]=[CH:44][C:45]([NH2:48])=[N:46][CH:47]=1>CN(C)C=O>[CH:7]1([CH2:12][C@H:13]([CH2:24][N:25]([CH:34]=[O:35])[O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:14]([N:16]2[C@H:20]([C:21]([NH:48][C:45]3[CH:44]=[CH:43][C:42]([F:41])=[CH:47][N:46]=3)=[O:23])[CH2:19][CH:18]=[N:17]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

6

반응물 4

HCID 13901-MethylimidazoleHCID 31297Methanesulfonyl chlorideHCID 27377012-Amino-5-fluoropyridineHCID 86706370(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 86706373(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide수율 56.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

1-Methylimidazole (59.6 μl, 0.747 mmol) was added into the solution of (55)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (150 mg, 0.374 mmol) in N,N-dimethylformamide (DMF) (2.7 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (30.4 μl, 0.392 mmol) was added dropwise at 0° C. To the reaction mixture was added 5-fluoro-2-pyridinamine (46.1 mg, 0.411 mmol). After stirring for 2 h 10 min at ambient temperature, the reaction solution was purified by RP-HPLC to yield (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (104 mg, 0.210 mmol, 56% yield). MS (ES+) m/z 496.0 (MH+).

후처리

  1. customthe reaction solution was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-b02e64a5b48d452188b240af1e532240
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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