Diisopropylethylamine → HCID 86613294, compound

HRID 1640179Notes

Reaction equation

HRID 1640179 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:23]=[C:22]4[C:17]([CH2:18][CH2:19][CH:20]([C:24](O)=[O:25])[CH2:21]4)=[CH:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:60][C:61]1[CH:62]=[C:63]([CH:73]=[C:74]([C:76]([F:79])([F:78])[F:77])[CH:75]=1)[CH2:64][NH:65][C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69]>CN(C=O)C.O>[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:23]=[C:22]4[C:17]([CH2:18][CH2:19][CH:20]([C:24]([NH:60][C:61]5[CH:62]=[C:63]([CH:73]=[C:74]([C:76]([F:77])([F:78])[F:79])[CH:75]=5)[CH2:64][NH:65][C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:25])[CH2:21]4)=[CH:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:2][CH2:3]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 589022317-({2-[(Cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidHCID 59735029tert-butyl N-{[3-amino-5-(trifluoromethyl)phenyl]methyl}carbamate

Product 1

HCID 86613294HCID 86613294, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (3.03 g, 8.61 mmol) in DMF (75 mL), was added DIPEA (4.50 mL, 25.8 mmol) and HATU (4.91 g, 12.9 mmol). The reaction mixture was allowed to stir at rt for 30 min, and then tert-butyl [3-amino-5-(trifluoromethyl)benzyl]carbamate (2.50 g, 8.61 mmol) was added. The reaction mixture was allowed to stir for 18 h. Water was added and the precipitate was filtered, washed with water and hexane and dried under vacuum. The residue was purified by column chromatography to give tert-butyl [3-({[7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbonyl}-amino)-5-(trifluoromethyl)benzyl]carbamate (3.80 g, 70.6%) as a yellow solid. LCMS: (FA) ES+ 625.6, ES− 623.4.

Workup

  1. stirringto stir for 18 h
  2. filtrationthe precipitate was filtered
  3. washwashed with water and hexane
  4. customdried under vacuum
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1201cbb113c74861b174915ef3a328be
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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