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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
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HRID 1530631 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 178432609HCID 178432609, 화합물

생성물 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]oxazepine수율 51.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-eb2fb0ba10e94aebb0b3acea21c04ff3
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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