Ammonium Chloride → HCID 11582260, compound

HRID 1676967Notes

Reaction equation

HRID 1676967 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2C3O[CH2:20][CH2:19][N:18]([C:23]4[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[C:17]=3[CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1)(O)=[O:2].[Cl-].[NH4+].O[N:33]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:54](=[O:57])([O-])O.[Na+]>CN(C)C=O.O.C(N(CC)CC)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:54]3[O:57][CH2:20][CH2:19][N:18]([C:23]4[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[C:17]=3[CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1)(=[O:2])[NH2:33]

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11524373HCID 11524373, compound

Product 1

HCID 11582260HCID 11582260, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

N-(4-carboxyphenyl)-4-(3-chloropyridin-2-yl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxamide (100 mg) obtained in Example 1-035 was dissolved in N,N-dimethylformamide (2 ml), ammonium chloride (65 mg), 1-hydroxybenzotriazole (56 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (70 mg) and triethylamine (0.20 ml) were added in this order, and the mixture was stirred at room temperature for 10 hours. After adding water and saturated sodium hydrogencarbonate solution to the reaction mixture, the mixture was partitioned by adding ethyl acetate. After ethyl acetate layer was washed with water, concentrated and dried, the concentrate was suspended in and washed with water, the white solid substance was collected by filtration and dried to obtain the title compound (80 mg).

Workup

  1. customthe mixture was partitioned
  2. additionby adding ethyl acetate
  3. washAfter ethyl acetate layer was washed with water
  4. concentrationconcentrated
  5. customdried
  6. washwashed with water
  7. filtrationthe white solid substance was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-32995ab0defc468d87b696f0a6859310
Source dataset
uspto-grants-2011_08
Patent number
US08008292B2

Reaction notes

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