Methylamine → N-((6-Amino-2-methyl-4-(2-(methylamino)-2-oxoethoxy)pyridin-3-yl)methyl)-1-benzyl-1H-pyrazole-4-carboxamide

HRID 928401Notes

Reaction equation

HRID 928401 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)=[O:12])=[C:4]([O:25][CH2:26][C:27]([OH:29])=O)[CH:3]=1.[CH3:30][NH2:31].C1COCC1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:17]=2)=[O:12])=[C:4]([O:25][CH2:26][C:27]([NH:31][CH3:30])=[O:29])[CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 580813552-(6-Amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetic acid

Product 1

HCID 58081255N-((6-Amino-2-methyl-4-(2-(methylamino)-2-oxoethoxy)pyridin-3-yl)methyl)-1-benzyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(6-amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetic acid (35 mg, 0.051 mmol) was dissolved in DMF (1 ml), CDl (16.65 mg, 0.103 mmol) was added. After stirring for 15 min at rt Methylamin 2M in THF (0.257 ml, 0.513 mmol) was added and the reaction mixture was stirred 6 h at rt. Purification by prep HPLC (Nucleosil C18, 250×40 mm 5 to 100% ACN and 0.1% TFA, flow 40 mml/min.) offered the title compound. 1H-NMR (DMSO-d6, 400 MHz): 2.71 (d, 3H), 4.37 (d, 2H), 4.67 (s, 2H), 5.34 (s, 2H), 6.20 (s, 1H), 7.24 (m, 5H), 7.79 (s, 2H), 7.89 (s, 1H), 8.25 (d, 2H), 8.28 (s, 1H), 8.35 (t, 1H). HPLC/MS (Method B) Rtb=0.46 min, MS [M+H]+=409.4.

Workup

  1. additionCDl (16.65 mg, 0.103 mmol) was added
  2. additionwas added
  3. customPurification by prep HPLC (Nucleosil C18, 250×40 mm 5 to 100% ACN and 0.1% TFA, flow 40 mml/min
  4. customHPLC/MS (Method B) Rtb=0.46 min, MS [M+H]+=409.4

Sources & evidence

ORD record
ord-10a890b3451d40d1b3b5a16d9a8c31fd
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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