Hydrochloric Acid → 5-Amino-pyridine-2-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

HRID 1486753Notes

Reaction equation

HRID 1486753 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:14](=[O:36])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([C:29](=[O:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][CH2:24]3)[CH:17]=2)=[CH:12][CH:13]=1)(C)(C)C.Cl>O1CCOCC1>[C:31]([NH:30][C:29]([CH:26]1[CH2:25][CH2:24][N:23]([CH2:22][C:18]2[CH:17]=[C:16]([NH:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][N:10]=3)=[O:36])[CH:21]=[CH:20][CH:19]=2)[CH2:28][CH2:27]1)=[O:35])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118521983HCID 118521983, compound

Product 1

HCID 1185218555-Amino-pyridine-2-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of {6-[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester (1.21 g, 2.37 mmol) in dioxane (15 mL) is cooled to 0° C. and HCl 4M in dioxane (2.4 mL, 9.497 mmol) is added. The RM is stirred at RT for 1 h and then heated at 60° C. overnight. The red mixture is cooled down to RT and filtered. The filtercake is washed with dioxane (15 mL). The red solid residue is partitioned between DCM (15 mL) and aq.sat.NaHCO3 (15 mL). The aqueous phase is extracted twice with DCM (2×20 mL). The combined org phase are dried over MgSO4, filtered and concentrated until dryness. The title compound is obtained as a yellowish foam LC-MS C: tR=0.61 min; [M+H]+=410.4.

Workup

  1. temperatureheated at 60° C. overnight
  2. temperatureThe red mixture is cooled down to RT
  3. filtrationfiltered
  4. washThe filtercake is washed with dioxane (15 mL)
  5. customThe red solid residue is partitioned between DCM (15 mL) and aq.sat
  6. extractionThe aqueous phase is extracted twice with DCM (2×20 mL)
  7. dry with materialThe combined org phase are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated until dryness

Sources & evidence

ORD record
ord-d0d1b82dafc346fdb8e51ee954bbe6f7
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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