Triethylamine → 2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 524844Notes

Reaction equation

HRID 524844 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH2:4][CH2:3]1.[NH2:15][C:16]1[C:25]([C:26](O)=[O:27])=[C:19]2[N:20]=[CH:21][C:22]([F:24])=[CH:23][N:18]2[N:17]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC>CN1C(=O)CCC1.CCOC(C)=O>[NH2:15][C:16]1[C:25]([C:26]([NH:14][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[O:27])=[C:19]2[N:20]=[CH:21][C:22]([F:24])=[CH:23][N:18]2[N:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 203473Piperazine, 1-(3-amino-4-pyridyl)-4-methyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867208882-Amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 867208982-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-(4-methylpiperazin-1-yl)pyridin-3-amine (prepared according to methods similar to the one depicted in Preparation N-1, described below) (588.1 mg, 3.059 mmol), 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 5a (prepared according to methods similar to the ones depicted in the sequence Step 1-Step 2 of Preparation 2a) (500 mg, 2.549 mmol), TBTU (1.146 g, 3.569 mmol) and Et3N (515.9 mg, 710.6 μL, 5.098 mmol) in NMP (7 mL) was stirred at 110° C. in a sealed tube, for 20 h. The reaction mixture was diluted with EtOAc, washed with a saturated bicarbonate aqueous solution and brine. The organic was dried over MgSO4 and concentrated after filtration. The solid was triturated in DCM and then filtered off. It was further purified by Fractionlynx HPLC to yield the title compound as a colourless solid. MS (ES+) 371.3.

Workup

  1. customprepared
  2. customdepicted in Preparation N-1
  3. customprepared
  4. washwashed with a saturated bicarbonate aqueous solution and brine
  5. dry with materialThe organic was dried over MgSO4
  6. concentrationconcentrated
  7. filtrationafter filtration
  8. customThe solid was triturated in DCM
  9. filtrationfiltered off
  10. customIt was further purified by Fractionlynx HPLC

Sources & evidence

ORD record
ord-7218dad905094d969699ffca60c77a13
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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