Acetic Acid → HCID 21064710, compound

HRID 1243796Notes

Reaction equation

HRID 1243796 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:17]3[CH2:26][CH2:25][C:20]4(OCC[O:21]4)[CH2:19][CH2:18]3)=[CH:8][C:9]=2[O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[S:4][C:3]=1[C:27]([NH2:29])=[O:28].C(O)(=O)C.C([O-])(O)=O.[Na+]>O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:17]3[CH2:18][CH2:19][C:20](=[O:21])[CH2:25][CH2:26]3)=[CH:8][C:9]=2[O:11][CH2:12][C:13]([F:14])([F:16])[F:15])[S:4][C:3]=1[C:27]([NH2:29])=[O:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 21064671HCID 21064671, compound

Product 1

HCID 21064710HCID 21064710, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-amino-6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-(2,2,2-trifluoro-ethoxy)-thieno[2,3-b]pyridine-2-carboxylic acid amide as a white powder (0.940 g, 2.17 mmol) in a 4:1 mixture of acetic acid: H2O (20 mL) was heated to 80° C. for 4h then cooled to room temperature and made basic by the addition of a saturated aqueous solution of NaHCO3 which caused a solid to precipitate from solution. The solid was collected by filtration and dried under reduced pressure to provide 0.680 g (80.5%) of 3-amino-6-(4-oxo-piperidin-1-yl)-4-(2,2,2-trifluoro-ethoxy)-thieno[2,3-b]pyridine-2-carboxylic acid amide as a clear oil.

Workup

  1. customto precipitate from solution
  2. filtrationThe solid was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5f9a7dcd5954fe88f5e02e5ac25f89b
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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