Ethanol → HCID 23004010, compound

HRID 396712Notes

Reaction equation

HRID 396712 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1.[CH:22]([N:25]([CH:28]([CH3:30])[CH3:29])CC)([CH3:24])[CH3:23].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=C[CH:45]=[CH:46][C:41]=2N=N1.N1C2C(=CC(C3[CH2:70][CH2:69][O:68][C:67](=[O:71])[CH2:66]3)=CC=2)CCC1.[CH2:72](O)C>CCOCC>[O:19]=[C:17]([N:25]1[C:28]2[C:29](=[CH:41][CH:46]=[CH:45][CH:30]=2)[CH2:72][CH2:24][CH:22]1[CH:23]1[CH2:70][CH2:69][O:68][C:67](=[O:71])[CH2:66]1)[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:21])=[O:20])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23003977HCID 23003977, compound

Product 1

HCID 23004010HCID 23004010, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of [4-(3-o-tolyl-ureido)-phenyl}-acetic acid (310 mg) and diisopropylethylamine (310 mg) dimethylformamide (5 ml) was treated successively with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (450 mg), then (R/S) 4-(1,2,3,4-tetrahydro-quinolin-6-yl)-tetrahydro-pyran-2-one [250 mg, Reference Example 5(c)]. After standing at room temperature for 2 hours the mixture was partitioned between ethyl acetate (100 ml) and dilute hydrochloric acid (100 ml). The layers were separated and the organic layer was washed with water, dried and evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate to give a yellow gum. This was dissolved in the minimum volume of ethanol and the solution was then treated with ether to yield a yellow solid, which was collected by filtration and dried to give the title compound (80 mg) as a yellow solid. LC-MS: RT=3.74 minutes (100% total area by ELS); MS (ES+) 520 (MNa+).

Workup

  1. customthe mixture was partitioned between ethyl acetate (100 ml) and dilute hydrochloric acid (100 ml)
  2. customThe layers were separated
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customto give a yellow gum
  7. customto yield a yellow solid, which
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c0677e3385c34cf381d8840b4245771b
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

Loading…