Dicyclohexylcarbodiimide → HCID 10383890, compound

HRID 2056903Notes

Reaction equation

HRID 2056903 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-1fa879836db6409ba010aaded1ad8891
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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