Triethylamine → HCID 135991587, compound

HRID 2369840Notes

Reaction equation

HRID 2369840 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[C:17]([NH2:22])[C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:11][CH2:10]1.CC([N:27]([C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:41]=[C:40]([CH:42]=O)[NH:39][N:38]=2)=[CH:33][CH:32]=1)C(=O)[O-])(C)C>CN(C=O)C>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]3[N:21]=[C:42]([C:40]4[NH:39][N:38]=[C:37]([C:34]5[CH:35]=[CH:36][C:31]([NH2:27])=[CH:32][CH:33]=5)[CH:41]=4)[NH:22][C:17]=3[CH:16]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27635454-(4-Methylpiperazino)-1,2-benzenediamineHCID 86616955HCID 86616955, compound

Product 1

HCID 135991587HCID 135991587, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

Triethylamine (2.32 g, 23 mmol) was added to a solution of 4-(4-methylpiperazin-1-yl)-benzene-1,2-diamine as the tetra-hydrochloride salt in anhydrous DMF (11 mL) after five minutes, a solution of 1,1-dimethylethyl[4-(5-formyl-1H-pyrazol-3-yl)phenyl]carbamate in anhydrous DMF (2 mL) was added to the diamine. The reaction flask was left open to the air and heated to 65° C. After twelve hours the reaction was concentrated in vacuo and the residue purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the product (0.60 g, 70% yield). (Note that the BOC group was removed under the purification conditions.)

Workup

  1. waitThe reaction flask was left open to the air
  2. concentrationAfter twelve hours the reaction was concentrated in vacuo
  3. customthe residue purified on reverse phase

Sources & evidence

ORD record
ord-205cf98e6511476eb71473efb20a8d3e
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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