Diisopropylethylamine → HCID 57872112, compound

HRID 1972332Notes

Reaction equation

HRID 1972332 reaction equation
[Cl-].[CH:2]1([NH:5][C:6](=[O:39])[C@@H:7]([OH:38])[C@@H:8]([NH:12][C:13]([C@@H:15]2[CH2:19][C@@H:18]([O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[C:23]([N:33]4[CH:37]=[CH:36][CH:35]=[N:34]4)[CH:22]=3)[CH2:17][NH2+:16]2)=[O:14])[CH2:9][CH2:10][CH3:11])[CH2:4][CH2:3]1.[C:40]([NH:44][C:45](=[O:55])[NH:46][C@H:47]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:48](O)=[O:49])([CH3:43])([CH3:42])[CH3:41].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[C:40]([NH:44][C:45](=[O:55])[NH:46][C@@H:47]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:48]([N:16]1[CH2:17][C@H:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[N:24]=[C:23]([N:33]3[CH:37]=[CH:36][CH:35]=[N:34]3)[CH:22]=2)[CH2:19][C@H:15]1[C:13]([NH:12][C@@H:8]([CH2:9][CH2:10][CH3:11])[C@H:7]([OH:38])[C:6]([NH:5][CH:2]1[CH2:4][CH2:3]1)=[O:39])=[O:14])=[O:49])([CH3:43])([CH3:42])[CH3:41]

Participants

7

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 51690949HCID 51690949, compoundHCID 86634502HCID 86634502, compound

Product 1

HCID 57872112HCID 57872112, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of (2S,4R)-2-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidinium chloride (6.3 g, 11.2 mmol) in dimethylsulfoxide (20 mL) was added (R)-2-(3-tert-butylureido)-3,3-dimethylbutanoic acid (2.33 g, 10.2 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 4.74 g, 12.1 mmol) followed by diisopropylethylamine (4.95 g, 38.4 mmol), and the reaction mixture was stirred at room temperature for 3 hours under nitrogen atmosphere. Completion of the reaction was monitored by TLC analysis. The reaction mixture was diluted with water and the resulting solid was filtered and dried under reduced pressure to yield 6.3 g (71.6%) of (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-2-carboxamide (HPLC purity: 99.2% by area; HPLC retention time: 15.06 minutes).

Workup

  1. filtrationthe resulting solid was filtered
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-df68751649eb4607aea20604ee7bf55b
Source dataset
uspto-grants-2013_04
Patent number
US08431733B2

Reaction notes

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