1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11512898, compound

HRID 504144Notes

Reaction equation

HRID 504144 reaction equation
[NH2:1][C@:2](C1CCOCC1)([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[C:3]([NH2:5])=[O:4].[F:23][C:24]([F:44])([F:43])[C:25]1[CH:26]=[C:27]([S:31]([N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]2[C:40](O)=[O:41])(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.[C:45](=[O:48])(O)[O-].[Na+].[CH:50]1[CH:55]=NC2N(O)N=N[C:52]=2[CH:51]=1.CCN=C=NCCCN(C)C>ClCCl>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([CH2:6][C@H:2]([NH:1][C:40]([C@@H:35]2[CH2:36][CH2:37][CH2:38][CH2:39][N:34]2[S:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:43])[F:44])[CH:26]=2)(=[O:33])=[O:32])=[O:41])[C:3](=[O:4])[NH:5][CH:50]2[CH2:55][CH2:45][O:48][CH2:52][CH2:51]2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 59428653HCID 59428653, compoundHCID 66750693HCID 66750693, compound

Product 1

HCID 11512898HCID 11512898, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 90 mg (0.29 mmol) of (S)-2-amino-3-(3,4-dimethoxy-phenyl)-(tetrahydropyran-4-yl)-propionamide and 98 mg (0.29 mmol) of (S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carboxylic acid in 2 ml of dichloromethane was added 25 mg (0.29 mmol) of sodium bicarbonate followed by 40 mg (0.29 mmol) of HOAT and 56 mg (0.29 mmol) of EDCI. The mixture was stirred at room temperature for 17 hours after which it was purified by flash chromatography on silica gel, eluting with 50-100% ethyl acetate/heptane to give 0.162 g (0.25 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.00-1.40 (m, 7H); 1.84 (b, 2H); 2.12 (bd, 1H); 2.60 (t, 1H); 2.99 (dd, 1H); 3.18 (dd, 1H); 3.45 (t, 2H); 3.61 (bd, 1H); 3.79-4.00 (m, 9H); 4.38 (b, 1H); 4.62 (q, 1H); 5.96 (d, 1H); 6.74-6.83 (m, 4H); 7.70 (t, 1H); 7.87 (d, 1H); 8.00 (d, 1H); 8.07 (s, 1H).

Workup

  1. customwas purified by flash chromatography on silica gel
  2. washeluting with 50-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-dfc5032997ba437db7be74466ce34c15
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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