Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 59785213, compound

HRID 470320Notes

Reaction equation

HRID 470320 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][N:4]([C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)[N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([NH:40][C:7]([C:6]3[C:2]([NH2:1])=[N:3][N:4]([C:10]4[N:15]=[C:14]([C:16]5[CH:17]=[CH:18][C:19]([N:22]([CH3:23])[CH3:24])=[CH:20][CH:21]=5)[CH:13]=[CH:12][N:11]=4)[CH:5]=3)=[O:9])=[CH:38][CH:39]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 242554804-[2-(4-Methylpiperazin-1-yl)ethyl]anilineHCID 59785015HCID 59785015, compound

Product 1

HCID 59785213HCID 59785213, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-Amino-1-[4-(4-dimethylamino-phenyl)-pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid (35 mg, 0.108 mM) diisopropylethylamine (70 ul, 0.402 mM), 4-[2-(4-Methyl-piperazin-1-yl)-ethyl]-phenylamine (30 mg, 0.1369 mM) in DMF (1 ml) to which was added HBTU (60 mg, 0.1583 mM) and the stirred 16 hr at room temperature. The resulting suspension was filtered and the solid washed with water (1×1 ml) and dried in vacuo to afford 3-Amino-1-[4-(4-dimethylamino-phenyl)-pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid {4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-amide (13 mg, 21% yield). ES-MS MH+526.7. The filtrate may be purified via RP-HPLC 0.1% TFA to afford additional material.

Workup

  1. customthe stirred 16 hr
  2. customat room temperature
  3. filtrationThe resulting suspension was filtered
  4. washthe solid washed with water (1×1 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7f8960a17a3040ce8c604167d6625a7b
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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