Diisopropylethylamine → [4,6-Dimethyl-5-({[1-(4-pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carbonyl]-amino}-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928368Notes

Reaction equation

HRID 928368 reaction equation
[N:1]1([CH2:6][C:7]2[CH:21]=[CH:20][C:10]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([OH:19])=O)[N:14]=[CH:13]3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:22]([O:26][C:27](=[O:39])[NH:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([CH2:36][NH2:37])=[C:31]([CH3:38])[N:30]=1)([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:22]([O:26][C:27](=[O:39])[NH:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([CH2:36][NH:37][C:17]([C:15]2[N:14]=[CH:13][N:12]([CH2:11][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][N:1]4[CH:5]=[CH:4][CH:3]=[N:2]4)=[CH:21][CH:20]=3)[CH:16]=2)=[O:19])=[C:31]([CH3:38])[N:30]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamideHCID 580812291-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 58081281[4,6-Dimethyl-5-({[1-(4-pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carbonyl]-amino}-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-Pyrazol-1-ylmethyl-benzyl)-1H-imidazole-4-carboxylic acid (0.67 g, 2.4 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.61 g, 2.4 mmol), HATU (1.8 g, 4.8 mmol) and DIPEA (1.3 mL, 7.2 mmol) in 10 mL DMF was stirred at room temperature for 16 h. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1 N aq. HCl. The organic layer was dried over MgSO4 and evaporated in vacuo. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min). LCMS (method A) RtA=1.418 min; [M+H]+=516.1.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1 N aq. HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)
  6. customLCMS (method A) RtA=1.418 min

Sources & evidence

ORD record
ord-d57da4a786e143dc8a6d5664d54a7769
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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