(S)-2-Methylpyrrolidine-2-carboxamide → (25)-1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)-2-methylpyrrolidine-2-carboxamide

HRID 886411노트

반응식

HRID 886411 반응식
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](O)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6](C)=[N:5]1)([CH3:3])[CH3:2].[CH3:25][C@@:26]1([C:31]([NH2:33])=[O:32])[CH2:30][CH2:29][CH2:28][NH:27]1>>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[C:16]4[CH:19]=[N:20][C:21]([N:27]5[CH2:28][CH2:29][CH2:30][C@@:26]5([CH3:25])[C:31]([NH2:33])=[O:32])=[CH:22][C:15]=4[O:14][CH2:13][CH2:12][N:11]3[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 14829625(S)-2-Methylpyrrolidine-2-carboxamideHCID 178432612HCID 178432612, 화합물

생성물 1

HCID 58204456(25)-1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)-2-methylpyrrolidine-2-carboxamide

실험 절차

Following the procedures for Examples 339 and 408, 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol and (S)-2-methyl-pyrollidine-2-carboxylic acid amide were reacted. The crude product was passed down a Isolute SCX-2 column, eluting with methanol then 2M NH3 in methanol. The basic fractions were concentrated in vacuo and the resultant residue subjected to reverse phase HPLC (C18 column, gradient 15 to 75% Methanol in water+0.1% HCO2H). The appropriate fractions were evaporated to dryness, passed down an Isolute NH2 column, eluting with methanol then further triturated in diethyl ether to give 402 as a white solid. LCMS: RT=2.79 min, [M+H]+=423. 1H NMR 400 MHz (CD3OD) δ: 9.14 (1H, s), 7.93 (1H, s), 7.69 (1H, s), 6.05 (1H, s), 5.99 (1H, m), 4.51-4.50 (4H, m), 3.70 (1H, m), 3.57 (1H, m), 3.50 (1H, m), 2.36-2.33 (1H, m), 2.10-2.08 (2H, m), 1.63 (3H, s), 1.56 (6H, dd, J=6.63, 2.34 Hz)

후처리

  1. customwere reacted
  2. washeluting with methanol
  3. concentrationThe basic fractions were concentrated in vacuo
  4. customThe appropriate fractions were evaporated to dryness
  5. washeluting with methanol
  6. customthen further triturated in diethyl ether

출처 및 근거

ORD 기록
ord-730e5eb30c774f869950ee9a22d5c16a
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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