Diisopropylethylamine → HCID 68929461, compound

HRID 853653Notes

Reaction equation

HRID 853653 reaction equation
[CH:1]([O:14][C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]([C:25](O)=[O:26])=[C:17]2[CH2:28][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[C:30](=[O:31])[C:16]=12)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:51]=[CH:52][CH:53]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:64]([OH:67])(=[O:66])C.C(OC(=O)C(O[P:75]([CH2:84][CH2:85][NH2:86])([O:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[O:76])C)C.[CH3:88][CH2:89]N(C(C)C)C(C)C>CN(C=O)C>[CH2:88]([O:67][C:64](=[O:66])[CH:52]([CH3:51])[CH2:53][P:75]([CH2:84][CH2:85][NH:86][C:25]([C:18]1[C:19]2[CH:20]=[CH:21][CH:22]=[N:23][C:24]=2[C:15]([O:14][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:16]2[C:30](=[O:31])[N:29]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)[CH2:28][C:17]=12)=[O:26])([O:77][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)=[O:76])[CH3:89]

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 58928692HCID 58928692, compoundHCID 86593996HCID 86593996, compound

Product 1

HCID 68929461HCID 68929461, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 13.5 mg of 213 in 0.13 mL of DMF was stirred with HATU (20 mg, 0.052 mmol) at room temperature for 10 minutes. To this solution was added a premixed solution of 219 (28 mg, 0.078 mmol) of approximately 50% purity in 0.130 mL of DMF and DIEA (13.4 mg, 0.104 mmol). The reaction mixture was gently heated with a heat gun for 30 seconds and then the reaction was allowed to proceed at room temperature for 2 hours when LCMS demonstrated complete consumption of the carboxylic acid. The reaction mixture was loaded onto a silica gel column and purified with EtOAc-10% MeOH to provide 9.5 mg of 3-[(2-{[9-Benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-amino}-ethyl)-phenoxy-phosphinoyl]-2-methyl-propionic acid ethyl ester 220 which was carried on to the next step.

Workup

  1. temperatureThe reaction mixture was gently heated with a heat gun for 30 seconds
  2. customconsumption of the carboxylic acid
  3. custompurified with EtOAc-10% MeOH

Sources & evidence

ORD record
ord-851e88a4686b4dce9f8559e156826c56
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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