Diisopropylethylamine → HCID 58902364, compound

HRID 1640198Notes

Reaction equation

HRID 1640198 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH:19]([C:23](O)=[O:24])[CH2:20]4)=[CH:15][CH:14]=3)[C:5]=2[CH:4]=[CH:3]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:59][C:60]1[CH:61]=[C:62]([CH:72]=[C:73]([C:75]([F:78])([F:77])[F:76])[CH:74]=1)[CH2:63][NH:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68]>CN(C=O)C.O>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH:19]([C:23]([NH:59][C:60]5[CH:61]=[C:62]([CH:72]=[C:73]([C:75]([F:76])([F:77])[F:78])[CH:74]=5)[CH2:63][NH:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:24])[CH2:20]4)=[CH:15][CH:14]=3)[C:5]=2[CH:4]=[CH:3]1

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 58902304HCID 58902304, compoundHCID 59735029tert-butyl N-{[3-amino-5-(trifluoromethyl)phenyl]methyl}carbamate

Product 1

HCID 58902364HCID 58902364, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-[(7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (0.18 g, 0.00053 mol) in DMF (5.3 mL) was added diisopropylethylamine (0.11 mL, 0.00063 mol) and HATU (0.24 g, 0.00063 mol). The reaction mixture was allowed to stir at rt for 1 hr. tert-Butyl [3-amino-5-(trifluoromethyl)benzyl]-carbamate (0.15 g, 0.00053 mol) was added and the reaction mixture was allowed to stir for an additional 15 hr. Water was added to the reaction mixture and a solid precipitated. This solid was collected by filtration and purified by column chromatography to give tert-butyl [3-[({7-[(7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate as a white solid (0.24 g, 75%). LCMS: (FA) ES+ 609.4.

Workup

  1. stirringto stir for an additional 15 hr
  2. customa solid precipitated
  3. filtrationThis solid was collected by filtration
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-b5cbd075270d43f2b155c8f6492feecc
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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