Sodium Hydroxide → HCID 90421848, compound

HRID 919373Notes

Reaction equation

HRID 919373 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])(=[O:14])=[O:13])[C:7](=[O:25])[C@@:6]2([NH:35][C:36]([N:38]1[CH2:43][CH2:42][N:41]([CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:40][CH2:39]1)=[O:37])[C:26]1[C:27]([O:32][CH2:33][CH3:34])=[N:28][CH:29]=[CH:30][CH:31]=1)#[N:2].[O:50]1[CH2:53][C:52](=O)[CH2:51]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[Na].[OH-].[Na+]>ClCCl.O.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])(=[O:14])=[O:13])[C:7](=[O:25])[C@@:6]2([NH:35][C:36]([N:38]1[CH2:43][CH2:42][N:41]([CH:44]2[CH2:45][CH2:46][N:47]([CH:52]3[CH2:53][O:50][CH2:51]3)[CH2:48][CH2:49]2)[CH2:40][CH2:39]1)=[O:37])[C:26]1[C:27]([O:32][CH2:33][CH3:34])=[N:28][CH:29]=[CH:30][CH:31]=1)#[N:2]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 5360545SodiumHCID 150242543-OxetanoneHCID 90421973HCID 90421973, compound

Product 1

HCID 90421848HCID 90421848, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a 100 ml 3-necked flask, 100 mg (0.145 mmol) of (S)—N-(5-cyano-1-((2,4-dimethoxyphenyl)sulfonyl)-3-(2-ethoxypyridin-3-yl)-2-oxoindolin-3-yl)-4-(piperidin-4-yl)-piperazine-1-carboxamide were stirred in 4 ml of dichloromethane. 10.45 mg (0.145 mmol) of oxetan-3-one dissolved in 2 ml of dichloromethane were added and the mixture was stirred for 5 min. 30.7 mg of Na2SO4 were added and the mixture was stirred for another 5 min. 17.41 mg of acetic acid were added and the reaction was stirred for another 30 min. 46.1 mg (0.217 mmol) of sodium triacetoxyhydroborate were added and the reaction was stirred overnight. 1 ml of 2N NaOH and then 7 ml of water were added and the mixture was extracted thrice with ethylacetate and water. The organic phase was died over MgSO4 and the solvent was removed. The resulting crude product was subjected to flash chromatography (silica gel/gradient from 0 to 5% methanol in dichloromethane) to yield 26.4 mg (24.4%) of the title compound.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for another 5 min
  3. stirringthe reaction was stirred for another 30 min
  4. stirringthe reaction was stirred overnight
  5. extractionthe mixture was extracted thrice with ethylacetate and water
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-3bbd7f377cfe421c96a19cf0fb157007
Source dataset
uspto-grants-2016_03
Patent number
US09273036B2

Reaction notes

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