Diisopropylethylamine → HCID 178479737, compound

HRID 2306669Notes

Reaction equation

HRID 2306669 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]([OH:12])=O.[ClH:13].Cl.[NH2:15][C@@H:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[ClH:13].[N:18]12[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19]1)[C@@H:16]([NH:15][C:10]([C:2]1[NH:3][C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[N:1]=1)=[O:12])[CH2:17]2

Participants

7

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 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 178524851HCID 178524851, compound

Product 1

HCID 178479737HCID 178479737, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 3H-imidazo[4,5-b]pyridine-2-carboxylic acid (90 mg, 0.55 mmol) in DMF (4 mL) is added (R)-(+)-3-aminoquinuclidine dihydrochloride (0.11 g, 0.56 mmol), DIEA (0.25 g, 0.35 mL, 1.9 mmol) and HATU (0.21 g, 0.56 mmol). The mixture is stirred overnight at rt, diluted with CH2Cl2 (50 mL) and washed with 1 N NaOH (2×50 mL) followed by sat. aq. NaHCO3 (50 mL). The material is purified by passage through acidic ion exchange resin. The free base is taken up in 3 M HCl/MeOH (10 mL) and stirred for 1.5 hr. Isopropanol and Et2O are added and the solid is isolated by vacuum filtration to afford Example 1004 in 57% yield. MS for C14H17N5O: 272 (M+H)+.

Workup

  1. washwashed with 1 N NaOH (2×50 mL)
  2. customThe material is purified by passage through acidic ion exchange resin
  3. stirringstirred for 1.5 hr
  4. additionIsopropanol and Et2O are added
  5. customthe solid is isolated by vacuum filtration
  6. customto afford Example 1004 in 57% yield

Sources & evidence

ORD record
ord-309622c4ea304fa297b4be1ed5e8984e
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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