1-Pyrrolidineethanamine → HCID 86634753、化合物

HRID 911031ノート

反応式

HRID 911031 の反応式
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[ClH:25].[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][C:28]=1[O:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([NH:43][C:44]2[S:45][CH:46]=[C:47]([CH3:49])[N:48]=2)[CH:38]=1.[NH2:50][CH2:51][CH2:52][N:53]1[CH2:57][CH2:56][CH2:55][CH2:54]1.CN(C=O)C>O>[ClH:25].[ClH:25].[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:50][CH2:51][CH2:52][N:53]2[CH2:57][CH2:56][CH2:55][CH2:54]2)=[O:33])=[CH:29][C:28]=1[O:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([NH:43][C:44]2[S:45][CH:46]=[C:47]([CH3:49])[N:48]=2)[CH:38]=1

参加物

6

反応物 4

HCID 13441-PyrrolidineethanamineHCID 6228DimethylformamideHCID 2733179PyBroPHCID 866347544-Fluoro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride

生成物 1

HCID 86634753HCID 86634753、化合物収率 57.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 3 dram vial was charged with bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (0.488 g, 1.05 mmol), 4-fluoro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid hydrochloride (Example 107; 0.200 g, 0.524 mmol), N-(2-aminoethyl)pyrrolidine (0.179 g, 1.57 mmol) and DMF (3 mL). The reaction was stirred for 1 hour at ambient temperature. Water was added and the reaction was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography. 2M HCl in ether was added to the isolated material and the collected solids were dried over high vacuum to give the title compound (0.078 g, 28.9% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.21 (bs, 1H), 9.75 (bs, 1H), 8.86 (t, 1H), 8.23 (m, 1H), 7.92 (m, 2H), 7.64 (dd, 1H), 6.62 (m, 2H), 6.58 (d, 1H), 3.60 (m, 4H), 3.32 (quart, 2H), 3.03 (m, 2H), 2.21 (d, 3H), 2.00 (d, 2H), 1.85 (m, 2H).

後処理

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. addition2M HCl in ether was added to the isolated material
  7. customthe collected solids were dried over high vacuum

出典と根拠

ORDレコード
ord-1ccdaa9915ac42948c60989368c0aad4
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

反応ノート

読み込み中…