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Methanol → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(1-methyl-5-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1530631
ノート
印刷プレビュー

反応式

HRID 1530631 の反応式
C(O1[CH2:11][CH:10]([C:12]2[N:16]([CH3:17])[N:15]=[CH:14][C:13]=2[C:18]2[CH:19]=[C:20]3[C:29](=[CH:30][CH:31]=2)[C:28]2[N:24]([CH:25]=[C:26]([C:32]4[N:36]([CH:37]([CH3:39])[CH3:38])[N:35]=[C:34]([CH3:40])[N:33]=4)[N:27]=2)[CH2:23][CH2:22][O:21]3)[CH2:9][CH2:8][NH:7][C:6]1=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO>C1COCC1>[CH:37]([N:36]1[C:32]([C:26]2[N:27]=[C:28]3[C:29]4[CH:30]=[CH:31][C:18]([C:13]5[CH:14]=[N:15][N:16]([CH3:17])[C:12]=5[CH:10]5[CH2:9][CH2:8][N:7]([CH3:6])[CH2:11]5)=[CH:19][C:20]=4[O:21][CH2:22][CH2:23][N:24]3[CH:25]=2)=[N:33][C:34]([CH3:40])=[N:35]1)([CH3:39])[CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 178432609HCID 178432609、化合物

生成物 1

HCID 665588462-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(1-methyl-5-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine収率 51.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

A mixture of 1-tert-butyl-6-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazepan-2-one (150 mg, 0.269 mmol) and LiAlH4 (51 mg, 1.3 mmol) in THF (5 mL) was refluxed for 1 hr. MeOH was added to quench reaction, The solid was filtered off and the filtrate was evaporated to afford the crude product, which was purified by reverse phase Combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to give racemic 240 (65 mg, 51% yield), which was separated by chiral SFC (Cellulose-2 column, 10% MeOH (0.1% DEA) isocratic) to give: 22.5 mg of one enantiomer and 35.5 mg of the other (46% total yield). LCMS (ESI): RT=4.79 min, m/z: 473.4 [M+H+]. 1H-NMR (500 MHz, DMSO-d6) δ 8.41 (d, J=8.5 Hz, 1H), 7.90 (s, 1H), 7.52 (s, 1H), 7.12 (dd, J=1.5 Hz, J=8.5 Hz, 1H), 6.99 (s, 1H), 5.77 (t, J=7.0 Hz, J=13.5 Hz, 1H), 4.53 (s, 4H), 3.97 (s, 3H), 3.74 (s, 1H), 2.80-2.74 (m, 2H), 2.65 (t, J=9.5 Hz, J=18.5 Hz, 1H), 2.49-2.46 (m, 1H), 2.30 (s, 3H), 2.26 (s, 3H), 2.19-2.17 (m, 1H), 1.96-1.93 (m, 1H), 1.46 (s, 6H)

後処理

  1. temperaturewas refluxed for 1 hr
  2. customto quench
  3. customreaction
  4. filtrationThe solid was filtered off
  5. customthe filtrate was evaporated
  6. customto afford the crude product, which
  7. customwas purified by reverse phase Combiflash
  8. washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

出典と根拠

ORDレコード
ord-eb2fb0ba10e94aebb0b3acea21c04ff3
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

読み込み中…

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