Diisopropylethylamine → HCID 86721025, compound

HRID 524966Notes

Reaction equation

HRID 524966 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[CH2:24][N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.[NH2:32][C:33]1[C:42]([C:43]([NH:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][C:51]=2[CH:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)=[O:44])=[C:36]2[N:37]=[CH:38][C:39]([F:41])=[CH:40][N:35]2[N:34]=1.NC1[C:70]([C:71](ON2C3C=CC=CC=3N=N2)=[O:72])=C2N=CC(CC#N)=CN2N=1>CN1C(=O)CCC1>[NH2:32][C:33]1[C:42]([C:43]([NH:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][C:51]=2[CH:52]2[CH2:57][CH2:56][N:55]([C:71]([CH:70]3[CH2:28][CH2:26][N:25]([CH3:24])[CH2:29][CH2:31]3)=[O:72])[CH2:54][CH2:53]2)=[O:44])=[C:36]2[N:37]=[CH:38][C:39]([F:41])=[CH:40][N:35]2[N:34]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86721023HCID 86721023, compoundHCID 901998921H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 86721025HCID 86721025, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

TBTU (154.5 mg, 0.4812 mmol) and DIPEA (82.92 mg, 111.8 μL, 0.6416 mmol) were added to a solution of 2-amino-6-fluoro-N-[4-(4-piperidyl)-3-pyridyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (114 mg, 0.3208 mmol) and 1-methylpiperidine-4-carboxylic acid (Hydrochloric Acid (1)) (69.16 mg, 0.3850 mmol) in NMP (2.280 mL) and the resulting solution stirred at RT for 2 h. Passed through an SCX cartridge flushing the desired product with 2M ammonia in methanol and the filtrate concentrated in vacuo. The residue was purified by fractionlynx HPLC and the product fractions combined and freeze dried to leave 2-amino-6-fluoro-N-(4-(1-(1-methylpiperidine-4-carbonyl)piperidin-4-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a yellow crystalline solid. MS (ES+) 481.3.

Workup

  1. customPassed through an SCX cartridge flushing the desired product with 2M ammonia in methanol
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by fractionlynx HPLC
  4. customfreeze dried

Sources & evidence

ORD record
ord-6f6470b5f4134df0b4ef07a389513224
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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