1-Pyrrolidineethanamine → HCID 86634753, 화합물

HRID 911031노트

반응식

HRID 911031 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 86634753HCID 86634753, 화합물수율 57.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1ccdaa9915ac42948c60989368c0aad4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022222B2

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