(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile → 1{(S)-2-[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide

HRID 1869646

반응식

HRID 1869646 반응식
Br[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]#[N:11])=[O:4].[NH2:12][CH:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([NH2:23])=[O:22])=[O:15]>C1COCC1>[C:10]([C@@H:6]1[CH2:7][CH2:8][CH2:9][N:5]1[C:3](=[O:4])[CH2:2][NH:12][C@@H:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([NH2:23])=[O:22])=[O:15])#[N:11]

참가 물질

4

반응물 2

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrileHCID 197622411-(2-Amino-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid amide

생성물 1

HCID 99289781{(S)-2-[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide수율 74.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1-(2-bromo-acetyl)-(S)-pyrrolidine-2-carbonitrile (44 mg, 0.2 mmol) in THF (1 mL) was added slowly to a cold solution (−15° C.) of 1-(2-amino-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid amide (55 mg, 0.24 mmol) in THF (2 mL). The temperature of the reaction mixture was gradually increased to room temperature. After stirring at this temperature overnight, the residue was concentrated and purified by LCMS to yield 1{(S)-2-[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide (54 mg; 62%). This pure product (20 mg) was dissolved in THF (1 mL), HCl ether (0.1 mL; 2M) was added and the mixture was concentrated to give the HCl salt form of 1-{(S)-2-[2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide. 1H-NMR data (CDCl3—CD3OD, 20:1): δ, 8.25 and 6.25 (s, 1H each), 4.73 (m, 1H), 4.43 (t, 1H, J=5.4 Hz), 4.2 (d, 1H, J=14.1 Hz), 4.0-3.47 (m, 7H), 2.4-1.9 (m, 10H), 1.41 (m, 1H). MS: calculated for C18H29N5O3+H 364.2; found: 364.2.

후처리

  1. concentrationthe residue was concentrated
  2. custompurified by LCMS

출처 및 근거

ORD 기록
ord-bfd648cc78ae46c68e288b9739fdfe8b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638638B2

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