Diisopropylethylamine → HCID 68073646, compound

HRID 530882Notes

Reaction equation

HRID 530882 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](O)=[O:18])[CH:15]=3)[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)[N:9]=2)[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.[NH2:63][N:64]1[CH2:69][CH2:68][CH2:67][C:66]([CH2:78][OH:79])([CH2:70][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=2[F:77])[CH2:65]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:77][C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=1[CH2:70][C:66]1([CH2:78][OH:79])[CH2:67][CH2:68][CH2:69][N:64]([NH:63][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:9]=[C:8]3[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:18])[CH2:65]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 67983567HCID 67983567, compoundHCID 679849753-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid

Product 1

HCID 68073646HCID 68073646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask, 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (605 mg, 1.22 mmol), HATU (572 mg, 1.50 mmol) and (1-amino-3-(2-fluorobenzyl)piperidin-3-yl)methanol (258 mg, 0.94 mmol) was dissolved in dimethylformamide (3 mL). Diisopropylethylamine (0.819 mL, 4.7 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-a05dc466bedb4473b8d43b5d0d098eb5
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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