Toluene → HCID 53644824, compound

HRID 1068959Notes

Reaction equation

HRID 1068959 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:3]=1[C:18]#[N:19].C(O[CH:23](OCC)[N:24]([CH3:26])[CH3:25])C.C1(C)C=CC=CC=1>C(O)C>[C:11]([NH:10][CH2:9][CH2:8][NH:7][C:4]1[C:3]([C:18]#[N:19])=[C:2]([N:1]=[CH:23][N:24]([CH3:26])[CH3:25])[NH:6][N:5]=1)([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 1140TolueneHCID 70913Dimethylformamide diethylacetal2×HCID 21190627HCID 21190627, compound

Product 1

HCID 53644824HCID 53644824, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 76.3 9 (286.1 mmol) of 5-amino-3-[2-(Boc-amino)-ethylamino]-4cyano-pyrazole, 54 ml (315.1 mmol) of N,N-dimethylformamide diethyl acetal, 850 ml of toluene and 85 ml of ethanol is stirred at 100° C. for 5 hours. A further 24.5 ml (143 mmol) of N,N-dimethylformamide diethyl acetal are then added to the reaction mixture and stirring is continued for a further 3 hours at 100° C. After cooling to about 10° C., filtration and washing the filter residue with toluene and diethyl ether, 3-[2-(Boc-amino)-ethylamino]-4-cyano-5-(dimethylamino-methyleneamino)-pyrazole is obtained; m.p. 158-160° C.; ESI-MS: (M−H)−=320.

Workup

  1. stirringstirring
  2. waitis continued for a further 3 hours at 100° C
  3. temperatureAfter cooling to about 10° C.
  4. filtrationfiltration
  5. washwashing the filter residue with toluene and diethyl ether

Sources & evidence

ORD record
ord-becc6a96e24742b2bf3f37c4c15334c4
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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