Glycolic Acid → HCID 69046649, compound

HRID 2172882Notes

Reaction equation

HRID 2172882 reaction equation
[Cl:1][C:2]1[C:3]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][N:16]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[OH:23][CH2:24][C:25](O)=[O:26].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][N:16]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:24](=[O:23])[CH2:25][OH:26])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 757Glycolic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67508395HCID 67508395, compound

Product 1

HCID 69046649HCID 69046649, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(3-chloro-3′,5′-dimethyl-2,2′-bipyridin-6-yl)piperidin-4-amine (hydrochloride salt) (60 mg, 0.13 mmol) and 2-hydroxyacetic acid (14.8 mg, 0.20 mmol) in DMF (1.3 mL) were added (in this order) NMM (105 mg, 1.0 mmol), HOBT (26.3 mg, 0.20 mmol), and EDCI (38.5 mg, 0.20 mmol). The resulting solution was stirred at rt for 3.5 h. Water was added, and the mixture was stirred at rt overnight. Filtered off the solid that had crashed out, washed with water, and dried to get 23 mg (47%) of the title compound as a white solid. m/z (APCI+) for C19H23N4O2Cl 375.10 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.26 (s, 1 H) 7.67 (d, J=9.09 Hz, 1 H) 7.62 (d, J=8.34 Hz, 1H) 7.53 (s, 1 H) 6.93 (d, J=9.35 Hz, 1 H) 5.37 (t, J=5.94 Hz, 1 H) 4.18 (d, J=13.64 Hz, 2H) 3.82-3.94 (m, 1 H) 3.78 (d, J=5.81 Hz, 2 H) 2.91 (t, J=11.49 Hz, 2 H) 2.32 (s, 3 H) 2.08 (s, 3 H) 1.72 (dd, J=12.76, 2.91 Hz, 2 H) 1.41-1.54 (m, 2 H).

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. filtrationFiltered off the solid
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b46329993bdc4d11800c9b54284e8e1e
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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