Triethylamine → HCID 57818328, compound

HRID 1511456Notes

Reaction equation

HRID 1511456 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([O:19][C@H:20]3[CH2:24][N:23]([C:25](=[O:35])[C@@H:26]([NH:31][C:32](=[O:34])O)[C:27]([CH3:30])([CH3:29])[CH3:28])[C@H:22]([C:36]([O:38][CH3:39])=[O:37])[CH2:21]3)=[CH:9][C:10]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)=[N:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:47]([N:51]=C=O)([CH3:50])([CH3:49])[CH3:48]>ClCCl>[CH3:39][O:38][C:36]([C@@H:22]1[CH2:21][C@@H:20]([O:19][C:8]2[C:7]3[C:12](=[CH:13][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[N:11]=[C:10]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)[CH:9]=2)[CH2:24][N:23]1[C:25](=[O:35])[C@@H:26]([NH:31][C:32]([NH:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:34])[C:27]([CH3:28])([CH3:29])[CH3:30])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 68911701HCID 68911701, compound

Product 1

HCID 57818328HCID 57818328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1-((2S,4R)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)-2-(methoxycarbonyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamic acid hydrochloride (0.165 mmol) in dichloromethane (3.0 mL) was added triethylamine (0.06 mL, 0.413 mmol) and tert-butylisocyanate (0.02 mL, 0.165 mmol) and the reaction mixture was stirred at room temperature. After 16 hours, the reaction mixture was diluted with dichloromethane and washed with 1N HCl, saturated sodium bicarbonate, and brine. The dichloromethane layer was then evaporated to dryness to give (2S,4R)-methyl-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)-pyrrolidine-2-carboxylate.

Workup

  1. washwashed with 1N HCl, saturated sodium bicarbonate, and brine
  2. customThe dichloromethane layer was then evaporated to dryness

Sources & evidence

ORD record
ord-314346e70463447fb14b7025e4e7ce63
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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