(2S,4R)-4-methoxy-pyrrolidine-2-carboxylic acid amide → (2S,4R)-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)-4-methoxypyrrolidine-2-carboxamide

HRID 1629445노트

반응식

HRID 1629445 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][O:26][C@H:27]1[CH2:31][NH:30][C@H:29]([C:32]([NH2:34])=[O:33])[CH2:28]1>O>[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:30]5[CH2:31][C@H:27]([O:26][CH3:25])[CH2:28][C@H:29]5[C:32]([NH2:34])=[O:33])=[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

4

반응물 2

HCID 67050845(2S,4R)-4-methoxy-pyrrolidine-2-carboxylic acid amideHCID 178432612HCID 178432612, 화합물

생성물 1

HCID 58204938(2S,4R)-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)-4-methoxypyrrolidine-2-carboxamide수율 32%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Following the procedure 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 (2S,4R)-4-methoxy-pyrrolidine-2-carboxylic acid amide were reacted. The reaction mixture was diluted with water passed down an SCX-2 cartridge, washed with DCM, ethyl acetate and methanol and products eluted with 2M ammonia in methanol. Appropriate fractions were concentrated in vacuo and the resultant residue was triturated in diethyl ether and methanol, filtered and dried to give 407 as beige solid (45 mg, 32%). LCMS: RT=2.60 min, [M+H]+=439. 1H NMR 400 MHz (CDCl3) δ: 9.27 (1 H, s), 7.83 (1 H, s), 7.57 (1 H, s), 6.79 (1 H, br, s), 6.00 (1 H, s), 5.98 (1 H, m), 5.29 (1 H, br, s), 4.65 (1 H, dd, J=8.28, 4.87 Hz), 4.49-4.47 (2 H, m), 4.39-4.34 (2 H, m), 4.23 (1 H, t, J=5.53 Hz), 3.74 (1 H, dd, J=10.34, 5.70 Hz), 3.51-3.46 (1 H, m), 3.36 (3 H, s), 2.52-2.51 (1 H, m), 2.24-2.23 (1 H, m), 1.55-1.54 (6 H, m)

후처리

  1. customwere reacted
  2. washwashed with DCM, ethyl acetate and methanol and products
  3. washeluted with 2M ammonia in methanol
  4. concentrationAppropriate fractions were concentrated in vacuo
  5. customthe resultant residue was triturated in diethyl ether
  6. filtrationmethanol, filtered
  7. customdried

출처 및 근거

ORD 기록
ord-5a20383b420049de9cedee6fb8493b04
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785626B2

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