Hydrochloric Acid → HCID 178434396, compound

HRID 2360681Notes

Reaction equation

HRID 2360681 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:37]([CH3:38])=[N:36][N:35](C4CCCCO4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28]C4CCCCO4)=[CH:24][CH:23]=3)[CH:21]=2)=[O:15])[C:10]([CH3:51])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:9]1)=O)(C)(C)C.Cl>ClCCl>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[N:19]=[C:18]3[NH:35][N:36]=[C:37]([CH3:38])[C:17]3=[C:16]([C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]3([CH3:51])[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:15])[CH:21]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86680300HCID 86680300, compound

Product 1

HCID 178434396HCID 178434396, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methyl-4-{3-methyl-1-(tetrahydropyran-2-yl)-6-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carbonyl}-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester (300 mg) and HCl (4M in 1,4-dioxane, 104 μL) in dichloromethane (2 mL) was stirred at r.t. overnight. A solid precipitated during the reaction, which was filtered off and dried in air. The sticky solid was triturated with acetonitrile and filtered again, washed with acetonitrile and dried in air. 137 mg (64%) of the title compound were obtained as hydrochloride salt.

Workup

  1. customA solid precipitated during the reaction, which
  2. filtrationwas filtered off
  3. customdried in air
  4. customThe sticky solid was triturated with acetonitrile
  5. filtrationfiltered again
  6. washwashed with acetonitrile
  7. customdried in air

Sources & evidence

ORD record
ord-489f1ba28cfd424ca5909944291c6638
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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