Water → HCID 17961979, compound

HRID 349582Notes

Reaction equation

HRID 349582 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:12]([NH:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11](/[CH:33]=[CH:34]/[C:35]#[N:36])[CH:10]=[N:9]1.[F-].[Na+].O>O1CCCC1>[NH2:36][CH2:35][CH2:34][CH2:33][C:11]1[CH:10]=[N:9][N:8]([CH3:7])[C:12]=1[NH:13][C:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 17961962HCID 17961962, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17961979HCID 17961979, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of lithium aluminum hydride (32.6 g) in tetrahydrofuran (1.3 L) was added (2E)-3-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]-2-propenonitrile (101.6 g) under ice-cooling. The mixture was refluxed for 4 hours. After cooling on an ice bath, sodium fluoride (100 g) and water (100 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 4-(3-aminopropyl)-1-methyl-5-tritylamino-1H-pyrazole (88.9 g). 1H-NMR(DMSO-d6) δ1.00–1.22 (2H, m), 1.70–1.90 (2H, m), 2.15–2.35 (2H, m), 2,74 (3H, s), 5.70 (1H, s), 6.97 (1H, s), 7.10–7.38 (15H, m)

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 4 hours
  3. temperatureAfter cooling on an ice bath
  4. customThe insoluble materials were removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-304d96c3a6ab40a6b222b85273b50059
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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