Pyridine → HCID 10529800, compound

HRID 1839436Notes

Reaction equation

HRID 1839436 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([NH:8][C:9]1[C:10]([NH2:23])=[CH:11][C:12]([O:15][Si:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:14]=1)=[O:7])#[N:2].N1C=CC=CC=1.[CH:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([CH3:35])[CH3:34]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([NH:8][C:9]1[C:10]([NH:23][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][C:36]([CH:33]([CH3:34])[CH3:35])=[CH:37][CH:38]=2)=[CH:11][C:12]([O:15][Si:16]([CH3:21])([CH3:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27594864-Isopropylbenzoyl chlorideHCID 10499221HCID 10499221, compound

Product 1

HCID 10529800HCID 10529800, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of N1-(3-cyanobenzoyl)-4-(dimethyl-t-butylsiloxy)-1,2-benzenediamine (2.63 g, 7.17 nmmol) and CH2Cl2 (45 mL) at 0° C. was added pyridine (0.65 mL, 8.0 mmol) followed by a solution of the 4-isopropyl benzoyl chloride (10.1 mmol) in CH2Cl2 (90 mL). The reaction was allowed to warm to room temperature and stirred for 10 m. The reaction was diluted with CH2Cl2 (200 mL) and washed with sat. aq. NH4Cl (2×50 mL). The organic layer was MgSO4 dried filtered, and concentrated. The residue was chromatographed (10% EtOAc/hexanes to 20% EtOAc/hexanes) to give the title compound as a solid (3.04 g, 83%); IR(CHCl3): 2962, 1656, 1610, 1513, 1473, 1295 cm−1; NMR(300 MHz, CDCl3): δ0.16 (s, 6H), 0.95 (s, 9H), 1.29 (s, 3H), 1.31 (s, 3H), 3.00 (m, 1H), 6.68 (d, 1H, J=9.0), 6.86 (s, 1H), 7.38 (d, 2H, J=8.1), 7.50 (d, 1H, J=9.0), 7.61 (m, 1H), 7.81 (d, 1H, J=6.3), 7.89 (d, 2H, J=7.1), 8.16 (d, 1H, J=9.3), 8.29 (s, 1H), 8.58 (br s, 1H), 9.40 (br s, 1H); MS(FD): 513.1.

Workup

  1. washwashed with sat. aq. NH4Cl (2×50 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed (10% EtOAc/hexanes to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a325d0315b754e49af65b2bde961edbd
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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