Hydrochloric Acid → HCID 68437853, compound

HRID 656666Notes

Reaction equation

HRID 656666 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[S:26][C:10]3=[N:11][C:12]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:27])=[O:6])[CH2:3][CH2:2]1.CO.C1COCC1.Cl>CN(C=O)C>[ClH:16].[CH:1]1([NH:4][C:5]([C:7]2[S:26][C:10]3=[N:11][C:12]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:27])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 11575133HCID 11575133, compound

Product 1

HCID 68437853HCID 68437853, compoundYield 128.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-amino-5-chloro-4-methyl-6-(2-morpholin-4-yl-ethoxy)-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.800 g, 1.95 mmol) and MeOH (50 ml) is heated to 50° C. The mixture is treated with THF (5 ml) and DMF (5 ml). While still at 50° C., the mixture is acidified to pH1 with concentrated HCl. A homogeneous solution is formed. The solution is allowed to cool slowly to room temperature. During this time, a white precipitate is formed. This solid is collected by filtration and dried in the vacuum oven for 72 hours at 50° C. This affords the title compound as a white solid (0.562 g, 65%). Mass (m/z): 411.1 (M++1)-HCl, 445.1 (M+−1).

Workup

  1. customstill at 50° C.
  2. customA homogeneous solution is formed
  3. temperatureto cool slowly to room temperature
  4. customDuring this time, a white precipitate is formed
  5. filtrationThis solid is collected by filtration
  6. customdried in the vacuum oven for 72 hours at 50° C

Sources & evidence

ORD record
ord-25fce6dd25a84b65a55308a020ef0325
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

Loading…