Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]thieno[3,2-b]pyridine-2-carboxamide

HRID 335578Notes

Reaction equation

HRID 335578 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CN(C(ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:37](N(CC)C(C)C)(C)[CH3:38]>CN(C=O)C>[N:27]12[CH2:26][CH2:25][CH:24]([CH2:37][CH2:38]1)[C@@H:23]([NH:28][C:10]([C:2]1[S:1][C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=1)=[O:12])[CH2:22]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22047169Thieno[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 10125449N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]thieno[3,2-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

35 mg (0.20 mmol) of thieno[3,2-b]pyridine-2-carboxylic acid, 58.3 mg (0.29 mmol) of R-3-aminoquinuclidine dihydrochloride, 111.4 mg (0.29 mmol) of HATU, 138.8 mg (1.07 mmol) of N,N-diisopropylethylamine and 1.5 ml of DMF are reacted according to the general procedure (variant A). The reaction mixture is purified by preparative HPLC and then subjected to fine purification on silica gel 60 (mobile phase: dichloromethane/methanol/ammonia 90:9:1). 44 mg (78% of theory) of the title compound are isolated.

Workup

  1. customThe reaction mixture is purified by preparative HPLC
  2. customsubjected to fine purification on silica gel 60 (mobile phase: dichloromethane/methanol/ammonia 90:9:1)

Sources & evidence

ORD record
ord-47ae0f9e7a7740af81f46f7b4e4065e5
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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