4-Methylmorpholine → HCID 9923070, compound

HRID 1977414Notes

Reaction equation

HRID 1977414 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:4][C:3]=1[C:19]([OH:21])=O.O.O[N:24]1C2C=CC=CC=2N=N1.[NH4+].[Cl-].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:4][C:3]=1[C:19]([NH2:24])=[O:21]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9836772HCID 9836772, compound

Product 1

HCID 9923070HCID 9923070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 131C (96 mg, 0.3 mmol) in DMF (2 mL) is treated with 1-hydroxybenzotriazole hydrate (67 mg, 0.44 mmol), NH4Cl (61 mg, 1.14 mmol) and 4-methylmorpholine (100 μL, 0.9 mmol), cooled to 0° C., treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (86 mg, 0.45 mmol), warmed to room temperature, stirred overnight, poured into saturated NaHCO3, collected, washed with water and dried. The residue is recrystallized from methanol/toluene/hexanes to provide the title compound.

Workup

  1. temperaturewarmed to room temperature
  2. customcollected
  3. washwashed with water
  4. customdried
  5. customThe residue is recrystallized from methanol/toluene/hexanes

Sources & evidence

ORD record
ord-d6e576f2711647a4b850178c4b160403
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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