Hydrochloric Acid → HCID 69676371, compound

HRID 919638Notes

Reaction equation

HRID 919638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]3[C:25]([C:26]([O:28]C)=[O:27])=[CH:24][N:23]=[C:22]4[NH:30][CH:31]=[CH:32][C:21]=34)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]3[C:25]([C:26]([OH:28])=[O:27])=[CH:24][N:23]=[C:22]4[NH:30][CH:31]=[CH:32][C:21]=34)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86706483HCID 86706483, compound

Product 1

HCID 69676371HCID 69676371, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-methyl 4-((1-(2-((3,5-dichlorophenyl)amino)acetyl)piperidin-3-yl)amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (173 mg, 0.36 mmol, 1.0 eq) in CH3OH (20 mL) and water (10 mL) was added NaOH (73 mg, 1.82 mmol, 5.0 eq). The mixture was stirred at 80° C. for 10 h, cooled to rt, adjusted pH to 6 with HCl (1N) the aqueous layer was extracted with EtOAc (50 mL×3). The organic layer was separated and concentrated in vacuo to afford the title compound as a yellow solid which was used to next step without further purification (120 mg, yield: 71%) to use next step. 1H NMR (400 MHz, CD3OD) δ: 8.6˜88.63 (m, 1H), 7.37˜7.32 (m, 1H), 7.02˜6.95 (m, 1H), 6.6˜06.57 (m, 2H), 6.34 (s, 1H), 4.57˜4.41 (m, 1H), 4.10˜3.75 (m, 5H), 3.65˜0.362 (m, 1H), 2.22˜2.21 (m, 1H), 2.04˜1.79 (m, 3H). ESI-MS: 462.1 (M+H)

Workup

  1. temperaturecooled to rt
  2. extractionwas extracted with EtOAc (50 mL×3)
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b1a96369bae4ffab541574b37b78422
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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