Ammonia → HCID 53682000, compound

HRID 1368340Notes

Reaction equation

HRID 1368340 reaction equation
[CH:1]1[C:6]2[S:7][CH2:8][CH2:9][CH2:10][O:11][C:5]=2[C:4]([C:12]([OH:14])=O)=[CH:3][CH:2]=1.C1C=CC2N(O)N=[N:21]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>CN(C=O)C.C(OCC)(=O)C>[CH:1]1[C:6]2[S:7][CH2:8][CH2:9][CH2:10][O:11][C:5]=2[C:4]([C:12]([NH2:21])=[O:14])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18519016HCID 18519016, compound

Product 1

HCID 53682000HCID 53682000, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 7,8-dihydro-6H-5-oxa-9-thia-benzocycloheptene-4-carboxylic acid (16.5g, 78.4 mmol) in 100 mL DMF was added in succession solid HOBT (21.3g, 157.3 mmol), solid EDC hydrochloride (30.1 g, 157.0 mmol), and 25% aqueous ammonia (18 mL, 128.4 mmol). After stirring for 48 h, the reaction mixture was diluted with 200 mL ethyl acetate and washed with water, 1N HCl, saturated NaHCO3, saturated NH4Cl, and brine. Drying over Na2SO4 and concentration yielded the amide as a tan solid (10.5 g, 64%).

Workup

  1. washwashed with water, 1N HCl, saturated NaHCO3, saturated NH4Cl, and brine
  2. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-815b4cf358a44517a508fd7cce73e644
Source dataset
uspto-grants-2003_06
Patent number
US06573295B2

Reaction notes

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