Diisopropylethylamine → 5-benzyl-1-methyl-N-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)piperidine-3-carboxamide

HRID 1842059Notes

Reaction equation

HRID 1842059 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH2:25]([CH:32]1[CH2:37][N:36]([CH3:38])[CH2:35][CH:34]([C:39]([OH:41])=O)[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[N:42]1[CH:47]=[CH:46][C:45]([C:48]2[C:56]3[C:51](=[CH:52][CH:53]=[C:54]([NH2:57])[CH:55]=3)[N:50]([C:58]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[N:49]=2)=[CH:44][CH:43]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:25]([CH:32]1[CH2:37][N:36]([CH3:38])[CH2:35][CH:34]([C:39]([NH:57][C:54]2[CH:55]=[C:56]3[C:51](=[CH:52][CH:53]=2)[N:50]([C:58]([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[N:49]=[C:48]3[C:45]2[CH:44]=[CH:43][N:42]=[CH:47][CH:46]=2)=[O:41])[CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=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 576858103-(pyridin-4-yl)-1-trityl-1H-indazol-5-amineHCID 666092525-Benzyl-1-methylpiperidine-3-carboxylic acid

Product 1

HCID 666145865-benzyl-1-methyl-N-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)piperidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (0.11 mmol) was added to a suspension of 5-benzyl-1-methylpiperidine-3-carboxylic acid (0.1 mmol) in DMF (0.5 mL) and was stirred at room temperature for 15 minutes. A solution of 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (0.1 mmol) in DMF (0.5 mL) was added to the reaction and followed by diisopropyl ethyl amine (DIEA) (0.1 mL). The mixture was stirred at room temperature for an additional 30 minutes. The reaction was quenched with water (5 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, dried using anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was progressed to the next step without purification.

Workup

  1. stirringThe mixture was stirred at room temperature for an additional 30 minutes
  2. customThe reaction was quenched with water (5 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was progressed to the next step without purification

Sources & evidence

ORD record
ord-634d74eee42e44ea81b710ece6597ffa
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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