Morpholine → HCID 11775339, compound

HRID 505782Notes

Reaction equation

HRID 505782 reaction equation
[CH:1]1([C:7]2[C:8]3[S:24][C:23]([C:25]([O:27]C)=[O:26])=[CH:22][C:9]=3[N:10]([CH2:18][C:19](O)=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]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.B(Br)(Br)Br>CN(C=O)C.C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[S:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][C:9]=3[N:10]([CH2:18][C:19]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:20])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 8083MorpholineHCID 25134Boron tribromideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68469890HCID 68469890, compound

Product 1

HCID 11775339HCID 11775339, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Following the procedure described above for 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-phenyl-4N-thieno[3,2-b]pyrrole-2-carboxylic acid (step 3), treatment of a solution (0.08 M) of [6-cyclohexyl-2-(methoxycarbonyl)-5-phenyl-4H-thieno[3,2-b]pyrrol-4-yl]acetic acid in DMF with morpholine (1.1 eq.), DIEA (3 eq.) and HATU (1.1 eq.) followed by treatment of a solution (0.1 M) of the resulting residue in DCM with BBr3 (1 M solution in DCM, 3 eq.) gave a residue that was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 5 micron, 19×150 mm; flow: 17 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 60% A isocratic for 4 min, linear to 50% A in 2 min, linear to 40% in 2 min then isocratic for 2 min, linear to 35% A in 2 min isocratic for 1 min then linear to 30% A isocratic for 1 min then linear to 0% A in 3 min) to afford the title compound (43%) as a solid.

Workup

  1. customgave a residue that
  2. customwas purified by RP-HPLC (Conditions
  3. waitlinear to 50% A in 2 min
  4. waitlinear to 40% in 2 min
  5. waitisocratic for 2 min
  6. waitlinear to 35% A in 2 min isocratic for 1 min then linear to 30% A isocratic for 1 min
  7. waitthen linear to 0% A in 3 min

Sources & evidence

ORD record
ord-93f8fe0b9aa943a9aa7d91a17cf13e3a
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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