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4-tert-Butylbenzaldehyde → HCID 178440762, compound

HRID 493111
Notes
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Reaction equation

HRID 493111 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=2[NH2:21])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:22]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C(O)(C)C.[Pd]>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:30]2[NH:20][C:16]3=[N:17][CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[C:15]3[N:21]=2)=[CH:32][CH:33]=1)([CH3:25])([CH3:24])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 703244-tert-ButylbenzaldehydeHCID 576808304-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178440762HCID 178440762, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

4-(2,3-Diamino-pyridin-4-yl)-piperazine-1-carboxylic acid t-butyl ester (6) (368 mg, 1.3 mmol) was dissolved in isopropanol (9 ml) with Pd/C 10% (100 mg) and para-t-butyl benzaldehyde (324 mg, 2 mmol). The mixture was heated to 80° C. for 18 hours. MS showed the disappearance of the diamine starting material. The solvent was filtered through CELITE to remove the palladium, and the solvent was removed under vacuum. The residue was dissolved in NMP (4 ml), TFA (12 ml) was added and the reaction mixture was allowed to stir under nitrogen for 12 hours. MS showed the formation of the title product, and the TFA was removed under vacuum. The crude product-NMP mixture was purified by HPLC Method E to yield the title product 7 (320 mg (74%), 0.96 mmol). 1H NMR (DMSO-d6): δ 13.35 (bs, 1H), 8.75 (bs, 1H), 8.11 (dd, J=7.3 Hz, 2.1 Hz, 2H), 8.01 (d, J=6.2 Hz, 1H), 7.55 (dd, J=7.3 Hz, 2.1 Hz, 2H), 6.60 (d, J=6.2 Hz, 1H), 4.14 (m, 4H), 3.26 (m, 4H), 1.33 (s, 9H). MS (ESI-POS): [M+H]+=336.

Workup

  1. filtrationThe solvent was filtered through CELITE
  2. customto remove the palladium
  3. customthe solvent was removed under vacuum
  4. dissolutionThe residue was dissolved in NMP (4 ml)
  5. additionTFA (12 ml) was added
  6. customthe TFA was removed under vacuum
  7. customThe crude product-NMP mixture was purified by HPLC Method E

Sources & evidence

ORD record
ord-404c39cdc192416196970c38d3acd066
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07534796B2

Reaction notes

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