Toluene → HCID 178441139, compound

HRID 452981Notes

Reaction equation

HRID 452981 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(C)C=CC=CC=1>ClCCl.C(OCC)(=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178441179HCID 178441179, compound

Product 1

HCID 178441139HCID 178441139, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 20 mL vial, to a solution of 3-tert-butyl-1H-pyrazol-5-amine (150 mg, 1.078 mmol) in dichloromethane (2 mL) and triethylamine (0.180 mL, 1.293 mmol) was added (chloromethanetriyl)tribenzene (300 mg, 1.078 mmol). The reaction was stirred at 20° C. for 10 hours before toluene (5 mL) and ethyl acetate (10 mL) were added. The solid was filtered and the filtrate was concentrated to provide the crude title compound (320 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.95-1.02 (m, 9H) 4.82 (s, 1H) 5.75 (s, 1H) 7.15-7.37 (m, 15H) 11.13 (s, 1H); MS (DCI/NH3) m/z 382 (M+H)+.

Workup

  1. additionwere added
  2. filtrationThe solid was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-44f207ca23b84122bf2639d8036ca141
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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