Diisopropylethylamine → 2-methoxy-N-[1-methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethyl]acetamide

HRID 1098905Notes

Reaction equation

HRID 1098905 reaction equation
[CH3:1][CH:2]([NH2:26])[CH:3]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[N:9]=[CH:8]2.CCN(C(C)C)C(C)C.[CH3:36][O:37][CH2:38][C:39](Cl)=[O:40]>C(#N)C>[CH3:36][O:37][CH2:38][C:39]([NH:26][CH:2]([CH3:1])[CH:3]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[N:9]=[CH:8]2)=[O:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 668129981-Methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethylamine

Product 1

HCID 668129702-methoxy-N-[1-methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethyl]acetamideYield 29.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethylamine (118a, 14 mg, 0.041 mmol), DIPEA (12 ul, 0.070 mmol) and acetonitrile (2 ml) were charged in a 7 ml vial. Methoxyacetyl chloride (12 ul, 0.13 mmol) was added, the vial was sealed and the solution stirred (magnetic bar) at r.t. for 1 h. Concentration and purification on C18 (Kromasil) with acetonitrile:water:TFA, 45:55:0.1 to 90:10:0.1 over 30 min, afforded 5 mg (29%) of 2-methoxy-N-[1-methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethyl]acetamide.

Workup

  1. customthe vial was sealed
  2. concentrationConcentration and purification on C18 (Kromasil) with acetonitrile
  3. waitwater:TFA, 45:55:0.1 to 90:10:0.1 over 30 min

Sources & evidence

ORD record
ord-896a3e60e8c44f4996c86fdc7d0b6177
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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