2-Methoxyethylamine → HCID 59416171, compound

HRID 2061842Notes

Reaction equation

HRID 2061842 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([C:14]4[CH:15]=[N:16][C:17]([NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:18][C:19]=4[C:20]4[S:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:24]=4)=[CH:11][CH:12]=3)[C:7](=[O:35])[C:6]([C:36](O)=[O:37])=[CH:5]2)[CH2:3][CH2:2]1.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.[CH3:72][O:73][CH2:74][CH2:75][NH2:76]>CN(C=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([C:14]4[CH:15]=[N:16][C:17]([NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[CH:18][C:19]=4[C:20]4[S:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:24]=4)=[CH:11][CH:12]=3)[C:7](=[O:35])[C:6]([C:36]([NH:76][CH2:75][CH2:74][O:73][CH3:72])=[O:37])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59415783HCID 59415783, compound

Product 1

HCID 59416171HCID 59416171, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-cyclopropyl-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 20, 80 mg, 0.15 mmol) in DMF (3 mL) was added HATU (112 mg, 0.29 mmol), DIEA (0.051 mL, 0.29 mmol) followed by 2-methoxyethanamine (22.11 mg, 0.29 mmol). After 1 h stirring, LC-MS shows completion of reaction. DMF removed under vacuum, and the residue was purified by ISCO column using MeOH—CH2Cl2 (0-20%) to give white solid (47.3 mg, 53.5%).

Workup

  1. customcompletion of reaction
  2. customDMF removed under vacuum
  3. customthe residue was purified by ISCO column

Sources & evidence

ORD record
ord-5658527f8b894d229a7ae346181f8fbc
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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