Isobutyryl chloride → HCID 58724512, compound

HRID 1910124Notes

Reaction equation

HRID 1910124 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:24](=[O:31])[NH:25][C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[C:5]2[N:9]=[C:8]([NH:10][C:11]([C:13]3[N:14]=[CH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:12])[NH:7][C:6]=2[CH:23]=1.[C:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34]>N1C=CC=CC=1>[NH:30]1[CH:29]=[CH:28][N:27]=[C:26]1[NH:25][C:24]([C:4]1[C:5]2[N:9]=[C:8]([NH:10][C:11]([C:13]3[N:14]=[CH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:12])[NH:7][C:6]=2[CH:23]=[C:2]([NH:1][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:3]=1)=[O:31]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 58724420HCID 58724420, compound

Product 1

HCID 58724512HCID 58724512, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

20 mg (0.04 mmol) of isoquinoline-3-carboxylic acid [6-amino-4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide (Example 129) was dissolved in pyridine (2 mL). To this stirring solution at 0° C., 5.6 mg (0.053 mmol) of isobutyryl chloride was added in one portion. The reaction mixture was stirred for 10 min at 0° C. and warmed to room temperature. The pyridine was evaporated and water (5 mL) was added to the reaction mixture. The mixture was stirred for 10 min. and the resulting solid was filtered, washed with water (2 mL) and diethyl ether (5 mL), and dried to provide 15.5 mg (66.5%) of isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-6-isobutyrylamino-1H-benzoimidazol-2-yl]-amide. LCMS: 483 (M+1)+. 1H NMR (CD3OD, 400 MHz): δ 9.43 (s, 1H), 8.77 (s, 1H), 8.06-8.31 (m, 5H), 7.80-7.93 (m, 3H), 7.08 (s, 2H), 2.45 (m, 1H), 1.1 (d, 6H) ppm.

Workup

  1. temperaturewarmed to room temperature
  2. customThe pyridine was evaporated
  3. additionwater (5 mL) was added to the reaction mixture
  4. stirringThe mixture was stirred for 10 min.
  5. filtrationthe resulting solid was filtered
  6. washwashed with water (2 mL) and diethyl ether (5 mL)
  7. customdried

Sources & evidence

ORD record
ord-62ec3c60ee6443999ff65fbc862f31ae
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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