Acetic Acid → HCID 67003833, compound

HRID 2362638Notes

Reaction equation

HRID 2362638 reaction equation
[Cl:1][C:2]1[C:3]([C:29]2[S:33][C:32]([C:34]3([O:38][CH2:39][O:40][CH3:41])[CH2:37][CH2:36][CH2:35]3)=[N:31][CH:30]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH:17]=O)[CH:15]=3)[N:8]([S:19]([C:22]3[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:5]2=[N:6][CH:7]=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:53][NH:54][CH3:55].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[Cl:1][C:2]1[C:3]([C:29]2[S:33][C:32]([C:34]3([O:38][CH2:39][O:40][CH3:41])[CH2:35][CH2:36][CH2:37]3)=[N:31][CH:30]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH2:17][N:54]([CH3:55])[CH3:53])[CH:15]=3)[N:8]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=3)(=[O:21])=[O:20])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 86659280HCID 86659280, compound

Product 1

HCID 67003833HCID 67003833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)acetaldehyde (14C) (300 mg, 0.490 mmol) in tetrahydrofuran (3.267 mL) was added sequentially acetic acid (0.056 mL, 0.980 mmol), sodium sulfate (139 mg, 0.980 mmol) and dimethylamine (0.368 mL, 0.735 mmol). The reaction was stirred for 0.5 hours at ambient temperature, and sodium triacetoxyborohydride (208 mg, 0.980 mmol) was added in a single portion. The reaction was stirred overnight and then quenched by the addition of saturated aqueous sodium bicarbonate and ethyl acetate. The layers were separated, and the aqueous layer was extracted with addition ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the next step without further purification. MS ESI(+) m/z 641.2 [M+H]+.

Workup

  1. stirringThe reaction was stirred overnight
  2. customquenched by the addition of saturated aqueous sodium bicarbonate and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with addition ethyl acetate (2×)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2facb2494be54bbd8b3d337d2515a0dd
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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