Diisopropylethylamine → Methyl 2-(6-amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetate

HRID 928399Notes

Reaction equation

HRID 928399 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH2:10])=[C:4]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.[CH2:17]([N:24]1[CH:28]=[C:27]([C:29](O)=[O:30])[CH:26]=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH:10][C:29]([C:27]2[CH:26]=[N:25][N:24]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:28]=2)=[O:30])=[C:4]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 64838761-Benzyl-1H-pyrazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58081211HCID 58081211, compound

Product 1

HCID 58081178Methyl 2-(6-amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-(6-amino-3-(aminomethyl)-2-methylpyridin-4-yloxy)acetate (271 mg, 0.909 mmol), 1-benzyl-1H-pyrazole-4-carboxylic acid (synthesis description below) (184 mg, 0.909 mmol) and DIPEA (0.794 ml, 4.54 mmol) were dissolved in DMF (2 ml), then HATU (518 mg, 1.363 mmol) was added and the reaction mixture was stirred over night at rt. Purification by prep HPLC (Sun-Fire C18, 100×30mm 5 to 100% ACN and 0.1% TFA, flow 40 mml/min.) offered the titled compound after lyophilisation. HPLC (Method C) Rtc=2.789 min, MS (Method D): [M+H]+=410.0.

Workup

  1. customPurification by prep HPLC (Sun-Fire C18, 100×30mm 5 to 100% ACN and 0.1% TFA, flow 40 mml/min.)
  2. customHPLC (Method C) Rtc=2.789 min, MS (Method D)

Sources & evidence

ORD record
ord-afc23dc81a2449f4b51ca99e6712d1c6
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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