1-Hydroxybenzotriazole → N-{[4-(3-fluorobenzyl)morpholin-2-yl]methyl}-2-{4-[(methylsulfonyl)amino]phenyl}acetamide

HRID 2212021노트

반응식

HRID 2212021 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH2:13])[CH2:7]1.[CH3:17][S:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1)(=[O:20])=[O:19].ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH:13][C:29](=[O:30])[CH2:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][S:18]([CH3:17])(=[O:19])=[O:20])=[CH:27][CH:26]=2)[CH2:7]1

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27738874-(Methylsulphonylamino)phenylacetic acidHCID 16244559[4-(3-Fluorobenzyl)morpholin-2-yl]methylamine

생성물 1

HCID 21962840N-{[4-(3-fluorobenzyl)morpholin-2-yl]methyl}-2-{4-[(methylsulfonyl)amino]phenyl}acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
20 °C

실험 절차

A mixture of Intermediate 29 (0.0134 g), {4-[(methylsulfonyl)amino]phenyl}acetic acid (0.0137 g, known compound WO 9929655 A1), 1-hydroxybenzotriazole (0.0097 g) and N,N-diisopropylethylamine (0.01 ml) in N,N-dimethylformamide (0.5 ml) was treated with a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.00138 g) in N,N-dimethylformamide (0.5 ml). The mixture was stirred at 20° C. for 24 h. The mixture was partitioned between dichloromethane (4 ml) and saturated aqueous sodium hydrogen carbonate (4 ml). The phases were separated and the organic phase applied to an ion exchange cartridge (2 g Isolute SCX, prewashed with methanol). The SCX cartridge was eluted with methanol (10 ml) followed by 10% 0.880 ammonia in methanol (10 ml) and the appropriate fractions were concentrated in vacuo to give the title compoundas a colourless (0.0174 g).

후처리

  1. customThe mixture was partitioned between dichloromethane (4 ml) and saturated aqueous sodium hydrogen carbonate (4 ml)
  2. customThe phases were separated
  3. washThe SCX cartridge was eluted with methanol (10 ml)
  4. concentrationthe appropriate fractions were concentrated in vacuo
  5. customto give the title compoundas a colourless (0.0174 g)

출처 및 근거

ORD 기록
ord-6c7f7aae084f4e3e8f0990dc74bd352f
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101882B2

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