Pivaloyl chloride → HCID 136492440, compound

HRID 509021Notes

Reaction equation

HRID 509021 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:23])=[C:7]([C:9]2[NH:10][C:11](=[O:22])[N:12]([CH:14]3[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]3)[N:13]=2)[CH:8]=1.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C1COCC1.CCN(C(C)C)C(C)C>[Cl:23][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:8][C:7]=1[C:9]1[NH:10][C:11](=[O:22])[N:12]([CH:14]2[CH2:15][CH2:16][C:17]([CH3:20])([CH3:21])[CH2:18][CH2:19]2)[N:13]=1

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 136492384HCID 136492384, compound

Product 1

HCID 136492440HCID 136492440, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 5-(5-(aminomethyl)-2-chlorophenyl)-2-(4,4-dimethylcyclohexyl)-2H-1,2,4-triazol-3(4H)-one (Intermediate-73, 0.070 g, 0.202 mmol) in dry THF (5.0 mL), DIPEA (2.0 mL) and pivaloyl chloride (0.30 g, 0.242 mmol) were added and the reaction mass was stirred at RT for 16 h. After completion of the reaction, the reaction mass was quenched with water and extracted with 10% MeOH:DCM. The organic layer was washed with dilute HCl and concentrated. The obtained crude was purified with column chromatography on basic alumina by eluting with 2.0% MeOH:DCM to afford 0.040 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.44 (s, 6H), 1.47 (s, 9H), 1.81-1.94 (m, 8H), 3.86-3.90 (m, 1H), 4.40 (s, 2H), 7.33 (d, J=1.5 Hz, 1H), 7.45 (s, 1H), 7.50 (d, J=2.1 Hz, 1H), 8.16 (t, 1H), 11.93 (s, 1H); MS (m/z): 419.21 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched with water
  3. extractionextracted with 10% MeOH
  4. washThe organic layer was washed with dilute HCl
  5. concentrationconcentrated
  6. customThe obtained crude
  7. customwas purified with column chromatography on basic alumina
  8. washby eluting with 2.0% MeOH

Sources & evidence

ORD record
ord-a0fe2bdd5ae140d692ebc1da40533700
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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