Diisopropylethylamine → HCID 58418210, compound

HRID 588497Notes

Reaction equation

HRID 588497 reaction equation
[CH:1]1([NH:6][C:7](=[O:19])[NH:8][CH:9]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[O:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH:54]1[O:59][NH2:60]>CN(C=O)C>[CH:1]1([NH:6][C:7](=[O:19])[NH:8][CH:9]([C:11]2[S:15][C:14]([C:16]([NH:60][O:59][CH:54]3[CH2:55][CH2:56][CH2:57][CH2:58][O:53]3)=[O:18])=[CH:13][CH:12]=2)[CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58418235HCID 58418235, compound

Product 1

HCID 58418210HCID 58418210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 5-(1-(3-cyclopentylureido)ethyl)thiophene-2-carboxylic acid obtained in step 2 in DMF (1 mL) was added HATU (62 mg, 0.165 mmol) and N,N-diisopropylethylamine (130 μL, 0.75 mmol) was added a solution of O-(tetrahydropyran-2-yl)hydroxylamine (19.3 mg, 0.165 mmol) in N,N-dimethylformamide (1.0 mL). The reaction was stirred at room temperature for 12 hours. The solution was evaporated to dryness and to the residue was added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL). After separation, the aqueous layer was extracted with 1,2-dichloroethane (2×3 mL). The combined organic phases were evaporated to dryness to give crude 5-(1-(3-cyclopentylureido)ethyl)-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide. LC-MS: (FA) ES+382.

Workup

  1. customThe solution was evaporated to dryness and to the residue
  2. additionwas added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL)
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with 1,2-dichloroethane (2×3 mL)
  5. customThe combined organic phases were evaporated to dryness

Sources & evidence

ORD record
ord-9fecd9a9bc5b42bd8f7db36d75d5b31d
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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