3-Cyanobenzoyl chloride → HCID 52913685, compound

HRID 1887458Notes

Reaction equation

HRID 1887458 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[C:6]([N:8]([CH3:15])[C:9]2[CH:10]=[N:11][CH:12]=[N:13][CH:14]=2)[CH:7]=1.[C:17]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23])#[N:18]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:17]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH:16][C:4]1[CH:5]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[N:13][CH:12]=[N:11][CH:10]=2)[CH:7]=[C:2]([F:1])[CH:3]=1)=[O:23])#[N:18]

Participants

5

Reactant 2

HCID 3084833-Cyanobenzoyl chlorideHCID 58337710HCID 58337710, compound

Product 1

HCID 52913685HCID 52913685, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Compound 32 (15 mg, 0.069 mmol, 1.0 eq) was dissolved in CH2Cl2 (0.5 mL) and DMAP (9.2 mg, 0.075 mmol, 1.1 eq) was added and the reaction stirred for 5 min. 3-Cyanobenzoyl chloride (11 mg, 0.066 mmol, 1.0 eq) was added and the reaction was stirred until determination of completion by LCMS. The reaction was diluted with CH2Cl2, washed with water (1×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 6 mg (47%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.48 (s, 1H), 8.82 (s, 1H), 8.63 (s, 2H), 8.34 (s, 1H), (8.19 (d, J=8.0 Hz, 1H), 8.06 (d, J=7.8 Hz, 1H), 7.74 (t, J=7.8 Hz, 1H), 7.44 (d, J=11.0 Hz, 1H), 7.22 (s, 1H), 6.79-6.73 (m, 1H), 3.34 (s, 3H); ES-MS [M+1]+: 348.2.

Workup

  1. stirringthe reaction was stirred until determination of completion by LCMS
  2. washwashed with water (1×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b6a314522aef4ff0b6939da9c41114eb
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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