Diisopropylethylamine → Tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate

HRID 2080281Notes

Reaction equation

HRID 2080281 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:61][CH2:62][C:63]1[C:64]([CH2:69][NH:70][C:71](=[O:77])[O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[N:65][CH:66]=[CH:67][CH:68]=1>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:61][CH2:62][C:63]2[C:64]([CH2:69][NH:70][C:71](=[O:77])[O:72][C:73]([CH3:74])([CH3:76])[CH3:75])=[N:65][CH:66]=[CH:67][CH:68]=2)=[O:14])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575423046-(2-Cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acidHCID 57542432tert-butyl N-{[3-(aminomethyl)pyridin-2-yl]methyl}carbamate

Product 1

HCID 57542397Tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (0.60 g, 1.66 mmol) in DMF (3 mL) was added DIEA (0.329 mL, 2.53 mmol), HBTU (0.756 g, 2.00 mmol), then tert-butyl (3-(aminomethyl)pyridin-2-yl)methylcarbamate (0.473 g, 2.11 mmol). The reaction mixture was stirred at room temperature for 1 hr. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate as a pale yellow solid (545 mg, 57%). LRMS (M+H+) m/z 581.3.

Workup

  1. customThe crude mixture was purified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-daba292d518c455f8b9d9c6728f30ac4
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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