1-Hydroxybenzotriazole → HCID 66850251, compound

HRID 1948790Notes

Reaction equation

HRID 1948790 reaction equation
[CH3:1][Si:2]([CH3:24])([CH3:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:9]([C:20](O)=[O:21])=[CH:8]2.[NH2:25][C:26]1[CH:27]=[N:28][C:29]([N:32]2[CH2:35][CH:34]([OH:36])[CH2:33]2)=[CH:30][CH:31]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[OH:36][CH:34]1[CH2:35][N:32]([C:29]2[N:28]=[CH:27][C:26]([NH:25][C:20]([C:9]3[N:10]([CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=4)[C:11]4[C:7]([CH:8]=3)=[CH:6][CH:5]=[CH:4][C:3]=4[Si:2]([CH3:1])([CH3:23])[CH3:24])=[O:21])=[CH:31][CH:30]=2)[CH2:33]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574315251-(5-Aminopyridin-2-yl)azetidin-3-olHCID 58100944HCID 58100944, compound

Product 1

HCID 66850251HCID 66850251, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound No. 6 was prepared according to a process similar to that described in stage 5.4, by reacting 0.15 g (0.44 mmol) of 7-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid, prepared according to the protocol described in stage 5.3, with 109 mg (0.66 mmol) of 3-amino-6-(3-hydroxyazetidin-1-yl)pyridine, prepared according to the protocol described in stage 2.2, in the presence of 87 mg (0.44 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) and of 61 mg (0.44 mmol) of 1-hydroxybenzotriazole (HOBT) in 5 ml of dimethylformamide. 27 mg of the expected product are obtained.

Workup

  1. custom6 was prepared
  2. customprepared
  3. customprepared

Sources & evidence

ORD record
ord-da8310739a334817855f5cbda378fc23
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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