Diisopropylethylamine → (R)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid benzyl ester

HRID 737175Notes

Reaction equation

HRID 737175 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=O)[CH2:14][S:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:52][C:53]1[S:54][CH:55]=[C:56]([C:58]2[CH:69]=[CH:68][C:61]([C:62]([NH:64][CH:65]3[CH2:67][CH2:66]3)=[O:63])=[CH:60][CH:59]=2)[N:57]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16](=[O:18])[NH:52][C:53]2[S:54][CH:55]=[C:56]([C:58]3[CH:59]=[CH:60][C:61]([C:62](=[O:63])[NH:64][CH:65]4[CH2:67][CH2:66]4)=[CH:68][CH:69]=3)[N:57]=2)[CH2:14][S:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acidHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

Product 1

HCID 57849681(R)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-Thiazolidine-3,4-dicarboxylic acid 3-benzyl ester (52.5 mg, 0.20 mmol) was dissolved in DMF (2 mL). DIEA (68.5 μL, 0.39 mmol) was added followed by HATU (74.8 mg, 0.20 mmol). The reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (51.1 mg, 0.20 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 18.5 mg. MS: 509.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.54-0.75 (m, 4H), 2.78-2.90 (m, 1H), 4.51-4.59 (m, 1H), 4.62-4.70 (m, 1H), 4.83-5.18 (m, 3H), 7.07-7.43 (m, 5H), 7.77-7.99 (m, 5H), 8.39-8.47 (m, 1H), 12.55-12.64 (s, 1H).

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. filtrationThe reaction was filtered
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-fab90fcae1694212b57050207bde958f
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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