Dicyclohexylcarbodiimide → HCID 10383890, compound

HRID 586016Notes

Reaction equation

HRID 586016 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1[C:25]2[C:20](=[C:21]([CH2:26][C:27]([OH:29])=O)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1.ON1C2N=CC=CC=2N=N1.[F:40][C:41]([F:52])([F:51])[O:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>ClCCl.C(N(CC)CC)C>[CH:16]1[C:25]2[C:20](=[C:21]([CH2:26][C:27]([NH:48][CH2:47][C:46]3[CH:49]=[CH:50][C:43]([O:42][C:41]([F:40])([F:51])[F:52])=[CH:44][CH:45]=3)=[O:29])[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 5718464-(Trifluoromethoxy)benzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)

Product 1

HCID 10383890HCID 10383890, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

Polymer supported 1,3-dicyclohexylcarbodiimide (0.845 g) in dichloromethane (5 mL) was treated with 5-isoquinolinylacetic acid (0.075 g, 0.40 mmol) in dichloromethane (1 mL), 1-hydroxy-7-azabenzotriazole (0.049 g), and triethylamine (0.080 g) in dichloromethane (1 mL). After stirring for 5 minutes, the mixture was treated with 4-(trifluoromethoxy)benzylamine (0.40 mmol). After stirring for 16 hours, the mixture was treated with MP-Carbonate resin (0.310 g), stirred for 5 minutes, and filtered. The filtrate was diluted with dichloromethane (40 mL), washed with water (4×20 mL), brine (1×20 mL), dried (Na5SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound which was purified by forming the hydrochloride salt and triturating the solid with hot ethyl acetate. MS (ESI+) m/z 361 (M+H)+; MS (ESI−) m/z 359 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 3.99 (s, 2H), 4.31 (d, J 5.7, 2H), 7.31 (d, J 8.8, 2H), 7.36 (d, J 6.4, 2H), 7.66 (m, 2H), 7.93 (d, J 6.1, 1H), 8.03 (d, J 8.2, 1H), 8.51 (d, J 6.1, 1H), 8.74 (t, J 6.1, 1H), 9.31 (s, 1H); Anal. Calcd for C19H15F3N2O2+1 HCl: C, 57.51; H, 4.06; N, 7.06. Found: C, 57.42; H, 3.98; N, 6.72.

Workup

  1. stirringAfter stirring for 16 hours
  2. stirringstirred for 5 minutes
  3. filtrationfiltered
  4. additionThe filtrate was diluted with dichloromethane (40 mL)
  5. washwashed with water (4×20 mL), brine (1×20 mL)
  6. dry with materialdried (Na5SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-385e41d16e9e405397b272448e3af4c2
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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