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Phosphorus oxide (P4O10) → (+/-)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(5-methyl-1H-pyrazol-3-yl)-amino)-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 507079
Notes
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Reaction equation

HRID 507079 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:15](=O)[CH2:16][C:17](=O)[CH3:18])[C:9]2[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:8]1=2)=[O:6])([CH3:3])[CH3:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O.[NH2:56][NH2:57]>CCO>[F:35][C:32]([F:34])([F:33])[C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=1)[CH2:21][N:14]([C:15]1[CH:16]=[C:17]([CH3:18])[NH:57][N:56]=1)[CH:10]1[CH2:11][CH2:12][CH2:13][N:7]([C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:6])[C:8]2[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:9]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24654Hydrazine hydrate (1:1)HCID 59432322(+/-)-5-[(3,5-Bistrifluoromethyl-benzyl)-(3-oxo-butyryl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester

Product 1

HCID 11585133(+/-)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(5-methyl-1H-pyrazol-3-yl)-amino)-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateYield 21.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Add cold (ice bath) absolute EtOH (1 mL) slowly to a cooled 0° C. stirred mixture of (+/−)-5-[(3,5-bistrifluoromethyl-benzyl)-(3-oxo-butyryl)-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester (118 mg, 0.20 mmol) and phosphorus pentoxide (511 mg, 3.6 mmol). Then, add hydrazine hydrate (0.062 mL, 2.0 mmol) dropwise while keeping the mixture cooled at 0° C. Heat at 100° C. overnight in a sealed tube. Cool down the mixture and remove the solvents under reduce pressure. Partition the residue between water and dichloromethane. Separate the layers, and dry organic phase over anhydrous magnesium sulfate, filter and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, and then by a SCX cartridge to afford the title compound (25 mg, 21%). MS (ES+): 589 (M+H).

Workup

  1. temperatureHeat at 100° C. overnight in a sealed tube
  2. temperatureCool down the mixture
  3. customremove the solvents
  4. customPartition the residue between water and dichloromethane
  5. customSeparate the layers, and dry organic phase over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the residue by flash chromatography
  9. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-81ff922805f84b1c9f9622e75eeeb76f
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes