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Quinoline → benzyl 2-(7-methyl-1H-indazol-5-yl)-1-(1-neopentyl-1H-tetrazol-5-yl)ethylcarbamate

HRID 2099807
Notes
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Reaction equation

HRID 2099807 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:13]([NH:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.P(Cl)(Cl)(Cl)(Cl)Cl.N1C2C(=CC=CC=2)C=CC=1.[N-:48]=[N+:49]=[N-:50].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:13]2[N:15]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:50]=[N:49][N:48]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7047QuinolineHCID 24819Phosphorus pentachlorideHCID 33557Sodium AzideHCID 57794671HCID 57794671, compound

Product 1

HCID 57794590benzyl 2-(7-methyl-1H-indazol-5-yl)-1-(1-neopentyl-1H-tetrazol-5-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent
2×

Procedure

A solution of benzyl 3-(7-methyl-1H-indazol-5-yl)-1-(neopentylamino)-1-oxopropan-2-ylcarbamate (0.17 g, 0.402 mmol) in chloroform (0.5 mL) was added to a mixture of phosphorus pentachloride (0.17 g, 0.802 mmol) and quinoline (0.2 mL) in chloroform (1.0 mL). After stirring at room temperature for 2 h, the solvents were removed in vacuo. The crude mixture was dissolved in acetonitrile (2.0 mL) and treated with sodium azide (78 mg, 3.0 equiv). After stirring the mixture at 40° C. overnight, the solvents were removed and the crude mixture dissolved in methylene chloride which was washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography afforded 73 mg (40%, 2 steps). 1H-NMR (CD3OD, 500 MHz) δ 0.82 (s, 9H), 2.46 (s, 3H), 2.30-3.46 (m, 2H), 3.69 (d, J=14.3, 1H), 3.93 (d, J=14.3, 1H), 4.98-5.13 (m, 2H), 5.30 (m, 1H), 6.02 (d, J=8.9, 1H), 6.86 (s, 1H), 7.25-7.35 (m, 5H), 7.94 (s, 1H). Mass spec.: 448.19 (MH)+.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe crude mixture was dissolved in acetonitrile (2.0 mL)
  3. stirringAfter stirring the mixture at 40° C. overnight
  4. customthe solvents were removed
  5. dissolutionthe crude mixture dissolved in methylene chloride which
  6. washwas washed with water (2×), brine (2×)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customColumn chromatography afforded 73 mg (40%, 2 steps)

Sources & evidence

ORD record
ord-def3075f12db41bdb8894a6d650c61b4
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07569578B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes