Sodium hydride → HCID 90014275, compound

HRID 2279154Notes

Reaction equation

HRID 2279154 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[C:17]3[N:19]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[N:20]=[C:21]([CH3:22])[C:16]3=[C:15]([CH2:29][N:30]3[CH2:35][C:34]([CH3:37])([CH3:36])[NH:33][CH2:32][C:31]3([CH3:39])[CH3:38])[CH:14]=2)=[CH:9][CH:8]=1.[CH3:40][O:41][CH2:42][C:43](Cl)=[O:44]>C1COCC1>[CH3:40][O:41][CH2:42][C:43]([N:33]1[CH2:32][C:31]([CH3:39])([CH3:38])[N:30]([CH2:29][C:15]2[CH:14]=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][O:4][CH3:3])=[CH:12][CH:11]=3)[N:18]=[C:17]3[N:19]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[N:20]=[C:21]([CH3:22])[C:16]=23)[CH2:35][C:34]1([CH3:37])[CH3:36])=[O:44]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 90013940HCID 90013940, compound

Product 1

HCID 90014275HCID 90014275, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 16 mg sodium hydride (60% in mineral oil) in 2 ml of abs. THF were added 80 mg of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine and after 10 min 17 mg of 2-methoxyacetyl chloride were added. After 16 h at rt the reaction was quenched by the addition of water, the layers were separated and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried and concetrated in vacuo. 93 mg of the title compound were obtained.

Workup

  1. customAfter 16 h at rt the reaction was quenched by the addition of water
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. customThe combined organic layers were dried

Sources & evidence

ORD record
ord-71b29413ef7a4cfc81349b3897248200
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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