Hydrochloric Acid → HCID 49841779, compound

HRID 1968184Notes

Reaction equation

HRID 1968184 reaction equation
[CH:1]1([CH:4]([NH:8][CH2:9][C:10]2[C:18]3[C:17]([C:19]([O:21]C)=O)=[CH:16][CH:15]=[N:14][C:13]=3[N:12](C(OC(C)(C)C)=O)[CH:11]=2)[CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO>[CH:1]1([CH:4]([N:8]2[CH2:9][C:10]3=[CH:11][NH:12][C:13]4[C:18]3=[C:17]([CH:16]=[CH:15][N:14]=4)[C:19]2=[O:21])[CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67224209HCID 67224209, compound

Product 1

HCID 49841779HCID 49841779, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-tert-Butyl 4-methyl 3-((1-cyclopropyl-3-hydroxypropylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (50 mg, 0.12 mmol) was stirred in MeOH (3 mL) with 1N NaOH (1 mL) at rt for 16 h. The reaction was neutralized with 1N HCl and concentrated in vacuo. The residue was dissolved in DMF (3 mL). HATU (47 mg, 0.12 mmol) was added, and the reaction stirred at room temperature for 2 h. The solution was concentrated in vacuo and purified by preparative HPLC eluting with a gradient of 15% to 70% Solvent B in Solvent A to give 16 mg of the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 8.34 (d, 1H, J=4.8 Hz), 7.35 (d, 1H, J=4.8 Hz), 7.28 (s, 1H), 5.10 (AB q, 2H, J=76.4, 16.8 Hz), 4.08-4.20 (m, 1H), 3.59 (t, 2H, J=6.4 Hz), 2.02-2.14 (m, 2H), 1.17-1.30 (m, 1H), 0.73-0.79 (m, 1H), 0.42-0.54 (m, 2H), 0.24-0.33 (m, 1H). [M+H] found 272.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DMF (3 mL)
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by preparative HPLC
  5. washeluting with a gradient of 15% to 70% Solvent B in Solvent A

Sources & evidence

ORD record
ord-6eb41d3e3f3c4880a19d4644d324413d
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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