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

HRID 1530672Notes

Reaction equation

HRID 1530672 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:29]=[CH:28][C:10]2[C:11]3[N:12]([CH:16]=[C:17]([C:19]4[N:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[C:21]([CH3:27])[N:20]=4)[N:18]=3)[CH2:13][CH2:14][O:15][C:9]=2[CH:8]=1)=O.FC(F)(F)C(O)=O.[CH2:38]([N:45]1[CH2:50][CH2:49][CH2:48][CH:47]([NH:51][NH2:52])[CH2:46]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)C(C)C)(C)C.C(O)C>>[CH2:38]([N:45]1[CH2:50][CH2:49][CH2:48][CH:47]([N:51]2[C:5]([C:7]3[CH:29]=[CH:28][C:10]4[C:11]5[N:12]([CH:16]=[C:17]([C:19]6[N:23]([CH:24]([CH3:25])[CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=6)[N:18]=5)[CH2:13][CH2:14][O:15][C:9]=4[CH:8]=3)=[CH:4][CH:3]=[N:52]2)[CH2:46]1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 683128761-Benzyl-3-hydrazinylpiperidine trifluoroacetic acid saltHCID 68313024HCID 68313024, compound

Product 1

HCID 683131799-(1-(1-benzylpiperidin-3-yl)-1H-pyrazol-5-yl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Procedure

(E)-3-(dimethylamino)-1-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)prop-2-en-1-one (0.366 g, 0.000901 mol), 1-benzyl-3-hydrazinylpiperidine trifluoroacetic acid salt (0.376 g, 0.00135 mol), and N,N-Diisopropylethylamine (0.392 mL, 0.00225 mol) was mixed in Ethanol (9 mL, 0.2 mol). The reaction mixture was heated to reflux and was stirred overnight. LCMS showed complete conversion to desired product. The reaction mixture was cooled to room temperature and concentrated to dryness and purified by rHPLC to give 9-(1-(1-benzylpiperidin-3-yl)-1H-pyrazol-5-yl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux

Sources & evidence

ORD record
ord-2a52ff80fac4446bbda8ce3b8ddbd6cf
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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