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 1626113ノート

反応式

HRID 1626113 の反応式
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]

参加物

4

反応物 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

生成物 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-ylamine収率 82.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-b06a5a8f287c4a909a34d17f0ad89f59
出典データセット
uspto-grants-2014_07
特許番号
US08785436B2

反応ノート

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