Ammonia → HCID 11278372, compound

HRID 917778Notes

Reaction equation

HRID 917778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([C:18]([OH:20])=O)=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].N.C1C[N:25]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([C:18]([NH2:25])=[O:20])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2724699PyBOPHCID 236309084-[(3,4-Dichlorophenyl)amino]-1,6-dihydro-1-methyl-6-oxo-3-pyridinecarboxylic acid

Product 1

HCID 11278372HCID 11278372, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step A (234 mg) was dissolved in dichloromethane (5 mL) and ethanolic ammonia (2 M, 2.0 mL, 4.0 mmol): PyBOP (579 mg, 1.10 mmol) was added in one portion and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with acetic acid (ca. 0.5 mL), diluted with ethyl acetate (40 mL) and washed with water (2×10 mL) and saturated brine (10 mL). The organics were dried over magnesium sulfate, concentrated in vacuo and chromatographed on silica gel. Elution with dichloromethane-methanol (4:1) afforded 4-(3,4-Dichloro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide (28 mg, 12% yield) as a dark yellow-colored solid. An analytical sample was prepared by crystallization from methanol: m.p. >250° C.; 1H NMR (DMSO-d6, 400 MHz) δ10.38 (s, 1H), 8.30 (s, 1H), 7.85 (br s, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.45 (br s, 1H), 7.23 (dd, J=8.8, 2.4 Hz, 1H), 5.70 (s, 1H), 3.33 (s, 3H). Anal. Calcd./Found for C13H11Cl2N3O2: C, 50.02/50.02; H, 3.55/3.19; N, 13.46/13.21.

Workup

  1. customThe reaction mixture was quenched with acetic acid (ca. 0.5 mL)
  2. additiondiluted with ethyl acetate (40 mL)
  3. washwashed with water (2×10 mL) and saturated brine (10 mL)
  4. dry with materialThe organics were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel
  7. washElution with dichloromethane-methanol (4:1)

Sources & evidence

ORD record
ord-609b96573efc411faf792308dc4f61d0
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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