Trifluoroacetic acid → (4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

HRID 1626113노트

반응식

HRID 1626113 반응식
COC1C=CC(C([NH:24][C:25]2[O:26][CH2:27][C@H:28]([F:48])[C@:29]([C:32]3[CH:37]=[C:36]([NH:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH:35]=[CH:34][C:33]=3[F:47])([CH3:31])[N:30]=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[F:48][C@H:28]1[CH2:27][O:26][C:25]([NH2:24])=[N:30][C@@:29]1([C:32]1[CH:37]=[C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[O:45][CH3:46])[CH:35]=[CH:34][C:33]=1[F:47])[CH3:31]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71008803[bis-(4-methoxy-phenyl)-phenyl-methyl]-{(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amine

생성물 1

HCID 71008880(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine수율 82.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-{(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amine (49.8 mg, 76.6 μmol) in dichloromethane (2 ml) was treated at room temperature with trifluoroacetic acid (89.2 mg, 59.9 μl, 766 μmol), and the mixture was stirred for 15 hours. After evaporation at reduced pressure, the dark red residue was purified by chromatography on a silica-NH2 phase using a gradient of heptane/ethyl acetate=100:0 to 50:50 as the eluent. The (4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (22 mg, 82% yield) was obtained as a white foam. MS (ISP): m/z=348.2 [M+H]+.

후처리

  1. customAfter evaporation at reduced pressure
  2. customthe dark red residue was purified by chromatography on a silica-NH2 phase

출처 및 근거

ORD 기록
ord-b06a5a8f287c4a909a34d17f0ad89f59
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785436B2

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