Diisopropylethylamine → N-(3-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

HRID 530887Notes

Reaction equation

HRID 530887 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:11]3[C:16]=2[CH2:15][C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=3)[CH:5]=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:63][C:64]1[CH:80]=[CH:79][CH:78]=[CH:77][C:65]=1[CH2:66][C:67]1([CH2:74][O:75][CH3:76])[CH2:72][CH2:71][CH2:70][N:69]([NH2:73])[CH2:68]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:63][C:64]1[CH:80]=[CH:79][CH:78]=[CH:77][C:65]=1[CH2:66][C:67]1([CH2:74][O:75][CH3:76])[CH2:72][CH2:71][CH2:70][N:69]([NH:73][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:9]=[C:8]3[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:19])[CH2:68]1

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 679831693-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-amineHCID 866982503-(2-methylpyridin-4-yl)-1-trityl-4H-indazole-5-carboxylic acid

Product 1

HCID 68074196N-(3-(2-Fluorobenzyl)-3-(methoxymethyl)piperidin-1-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask, 3-(2-methylpyridin-4-yl)-1-trityl-4H-indazole-5-carboxylic acid (271 mg, 0.546 mmol), HATU (256 mg, 0.67 mmol) and 3-(2-fluorobenzyl)-3-(methoxymethyl)piperidin-1-amine (122 mg, 0.42 mmol) was dissolved in dimethylformamide (2 mL). Diisopropylethylamine (0.366 mL, 2.1 mmol) was added to the reaction. The reaction was allowed to stir for an additional 1 h. Upon completion, the reaction was quenched with water (10 mL). The water layer was extracted with ethyl acetate (20 mL) three times. The organic fractions were combined, dried with sodium sulfate, and concentrated to yield the crude product. The crude product was progressed to the next step without further purification.

Workup

  1. customUpon completion, the reaction was quenched with water (10 mL)
  2. extractionThe water layer was extracted with ethyl acetate (20 mL) three times
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7084a62d51b8425c849ab46b990b1ffd
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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