1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67540094, compound

HRID 1192317Notes

Reaction equation

HRID 1192317 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:22][C:21]([CH3:23])=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[NH:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@@H:25]([C:34]([OH:36])=O)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CO.C(O)(C(F)(F)F)=O.[Pd]>[C:40]([O:39][C:37](=[O:38])[NH:24][CH:25]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:34]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:22][C:21]([CH3:23])=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:36])([CH3:43])([CH3:42])[CH3:41]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67537500HCID 67537500, compound

Product 1

HCID 67540094HCID 67540094, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-Benzyl-piperazin-1-yl)-6-methylthieno[3,2-d]pyrimidine (65 mg, 0.20 mmol) in MeOH (10 mL) was added Pd/C (10%, 20 mg) and two drop of TFA. The mixture was stirred under H2 balloon for 4 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in DCM (6 mL) and TEA (2 mL), then Boc-D-Phe(4-Cl)—OH (59 mg, 0.20 mmol) was added, followed by HOBT (50 mg, 0.37 mmol) and EDCI (74 mg, 0.39 mmol). The mixture was stirred at room temperature for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to give the product {1-(4-chlorobenzyl)-2-[4-(6-methylthieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (60 mg, 59%). 1H NMR (CDCl3, 400 Hz) δ 8.54 (s, 1H), 7.28-7.26 (d, J=7.2 Hz, 2H), 7.17-7.15 (d, J=8.4 Hz, 2H), 7.08 (s, 1H), 5.37-5.35 9d, J=8.8 Hz, 1H), 4.86-4.84 (m, 1H), 3.87-3.57 (m, 7H), 3.24-3.22 (m, 1H), 3.00-2.98 (d, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 516.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in DCM (6 mL)
  4. stirringThe mixture was stirred at room temperature for 12 hours
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-8cb5d9269b4049f7b62a9bbebe23dca5
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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