Diisopropylethylamine → HCID 57849777, compound

HRID 737183Notes

Reaction equation

HRID 737183 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([OH:12])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:46][C:47]1[S:48][CH:49]=[C:50]([C:52]2[CH:63]=[CH:62][C:55]([C:56]([NH:58][CH:59]3[CH2:61][CH2:60]3)=[O:57])=[CH:54][CH:53]=2)[N:51]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10](=[O:12])[NH:46][C:47]1[S:48][CH:49]=[C:50]([C:52]2[CH:53]=[CH:54][C:55]([C:56](=[O:57])[NH:58][CH:59]3[CH2:61][CH2:60]3)=[CH:62][CH:63]=2)[N:51]=1)=[O:4]

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 10844912trans-2-Carbomethoxycyclopentane-1-carboxylic acidHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

Product 1

HCID 57849777HCID 57849777, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Rac-trans-cyclopentane-1,2-dicarboxylic acid monomethyl ester (86 mg) was dissolved in DMF (5 mL) and treated with HATU (1.1 eq. 214 mg) and DIEA (3 eq, 267 μL) and stirred for 15 minutes. Then 4-(2-amino-thiazol-4-yl)-N-cyclopropyl-benzamide (1 eq, 129.5 mg) was added and the mixture stirred at ambient temperature overnight. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. Yield 14 mg. MS: 414.5 (M+H+); H1-NMR (DMSO-d6): δ(ppm) 12.4 (s, 1H), 8.4 (m, 2H), 7.9-7.7 (m, 5H), 3.6 (s, 3H), 3.2 (m, 2H), 2.8 (m, 1H), 2.0 (m, 2H), 1.7 (m, 4H) 0.7-0.6 (m, 4H).

Workup

  1. stirringthe mixture stirred at ambient temperature overnight
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customthe solvents removed
  5. dissolutionThe resulting mixture was redissolved in 5 ml of 90% DMF
  6. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  7. customto give the product

Sources & evidence

ORD record
ord-83ce49824df34ca28fb2d4a1d02bd9ed
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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