Cyclobutanecarbonyl chloride → HCID 67001524, compound

HRID 1186236Notes

Reaction equation

HRID 1186236 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:21][CH2:20][N:10]3[C:11]4[N:19]=[CH:18][CH:17]=[CH:16][C:12]=4[NH:13][CH2:14][CH2:15][CH:9]3[CH2:8]2)=[CH:4][CH:3]=1.[CH:24]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25]1>ClCCl>[CH:24]1([C:28]([N:13]2[CH2:14][CH2:15][CH:9]3[CH2:8][N:7]([CH2:6][C:5]4[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:21][CH2:20][N:10]3[C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]2=3)=[O:29])[CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 67001538HCID 67001538, compound

Product 1

HCID 67001524HCID 67001524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 64C (97 mg, 0.31 mmol) in dichloromethane (2 mL) was added to cyclobutanecarbonyl chloride (0.048 mL, 0.42 mmol). The resulting, turbid solution was stirred at room temperature for 12 hours, and then the reaction was quenched by the addition of 20% Na2CO3 (1 mL). After 30 minutes, the mixture was made basic (pH˜9) by addition of 1 M NaOH (˜0.2 mL), diluted with water (3 mL) and extracted with CHCl3 (3×2 mL). The combined organic phases were dried over K2CO3 and concentrated: 1H NMR (300 MHz, CD3OD) δ ppm 1.58-2.02 (m, 5H), 2.06-2.44 (m, 4H), 2.68-3.26 (m, 6H), 3.42-3.65 (m, 3H), 3.96-4.47 (m, 2H), 6.82-7.11 (m, 3H), 7.17-7.58 (m, 3H), 8.08-8.32 (m, 1H); MS (DCI) m/z 395 (M+H)+.

Workup

  1. customthe reaction was quenched by the addition of 20% Na2CO3 (1 mL)
  2. waitAfter 30 minutes
  3. additionby addition of 1 M NaOH (˜0.2 mL)
  4. additiondiluted with water (3 mL)
  5. extractionextracted with CHCl3 (3×2 mL)
  6. dry with materialThe combined organic phases were dried over K2CO3
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7bc1773452d54628a06fbc1407a32598
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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