Methoxyacetyl chloride → N-{1-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperidin-4-yl}-2-methoxy-acetamide

HRID 1842002Notes

Reaction equation

HRID 1842002 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:4][C@@H:3]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]3)=[CH:13][CH:12]=2)[CH2:2]1.[CH3:25][O:26][CH2:27][C:28](Cl)=[O:29]>C1COCC1>[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:4][C@@H:3]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([NH:22][C:28](=[O:29])[CH2:27][O:26][CH3:25])[CH2:20][CH2:21]3)=[CH:23][CH:24]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 866953541-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperidin-4-ylamine

Product 1

HCID 71737175N-{1-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperidin-4-yl}-2-methoxy-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Intermediate M (75 mg, 0.23 mmol) in THF (1 mL) & TEA (0.128 mL, 0.92 mmol) was added Methoxy-acetyl chloride (0.042 mL, 0.46 mmol). The reaction was stirred for 10 min then quenched with MeOH and purified by reversed phase HPLC eluting with 0-60% MeCN in water (+0.1% TFA) to provide the title compound 252. (LC/MS method 16: ES+ m/z 398.4 [M+H]+, Rt=0.31 min)

Workup

  1. customthen quenched with MeOH
  2. custompurified by reversed phase HPLC
  3. washeluting with 0-60% MeCN in water (+0.1% TFA)

Sources & evidence

ORD record
ord-84f6fdd2e06e4e2bb700224f7dae6d86
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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