Hydroxylamine → 4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide

HRID 572629Notes

Reaction equation

HRID 572629 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14]([OH:16])=O)[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:58][OH:59].CN([CH:63]=[O:64])C>>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14]([NH:58][O:59][CH:38]2[CH2:37][CH2:36][CH2:35][CH2:63][O:64]2)=[O:16])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Participants

6

Reactant 5

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441556654-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

Product 1

HCID 866375484-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamideYield 55%

Procedure

4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.080 g, 0.21 mmol), HATU (0.095 g, 0.25 mmol), and diisopropylethylamine (0.073 mL, 0.42 mmol) were dissolved in DMF (2 mL) and stirred for 30 minutes. O-Tetrahydropyran-2-yl)hydroxylamine (0.049 g, 0.42 mmol) was added and the mixture was stirred at room temperature. After 30 minutes, LCMS showed complete conversion. Reaction was quenched by addition of water (5 mL) and the precipitate was filtered off, washed with water (2 mL) and hexane (5 mL) and dried to afford the title compound (0.055 g, 55%).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. waitAfter 30 minutes
  3. customReaction
  4. customwas quenched by addition of water (5 mL)
  5. filtrationthe precipitate was filtered off
  6. washwashed with water (2 mL) and hexane (5 mL)
  7. customdried

Sources & evidence

ORD record
ord-6e2604004e0f4aaf82d86d57b695d067
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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