Diisopropylethylamine → (S)-2-[(4-Cyano-2,6-difluorophenylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 18103

반응식

HRID 18103 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([F:26])[C:24]=1F)[C:20]#[N:21].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH:15][C:24]1[C:17]([F:16])=[CH:18][C:19]([C:20]#[N:21])=[CH:22][C:23]=1[F:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5938143,4,5-TrifluorobenzonitrileHCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate

생성물 1

HCID 67090562(S)-2-[(4-Cyano-2,6-difluorophenylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester수율 7.2%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.36 g) and 3,4,5-trifluorobenzonitrile (1.00 g) were heated under argon in xylene (10 ml) containing diisopropylethylamine (3.3 ml) for 16 h. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried and evaporated to give a solid which was triturated with pentane-ether to afford the title product (0.16 g) as an off white powder. Chromatography of the mother liquors on silica gel eluting with ethyl acetate-pentane mixtures afforded further title product (0.92 g). Mass Spectrum (API+): Found 252 (MH+-tBoc). C18H23F2N3O2 requires 351.

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. customdried
  5. customevaporated
  6. customto give a solid which
  7. customwas triturated with pentane-ether

출처 및 근거

ORD 기록
ord-9220fc6e22924dd5bda96f7b809804ba
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741329B2

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