4-Methylmorpholine → HCID 86646545, compound

HRID 2387244Notes

Reaction equation

HRID 2387244 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[C:16]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:15](=[O:25])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:26][C:27]([F:32])([F:31])[C:28]([O-:30])=[O:29].[CH:33]1([N:38]2[CH2:43][CH2:42][NH2+:41][CH2:40][C:39]2=[O:44])[CH2:37][CH2:36][CH2:35][CH2:34]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C.C(Cl)Cl>[F:26][C:27]([F:32])([F:31])[C:28]([O-:30])=[O:29].[CH:33]1([N:38]2[CH2:43][CH2:42][N:41]([C:4]([C:3]3[CH:7]=[C:8]([CH:9]=[CH:10][C:2]=3[F:1])[CH2:11][C:12]3[CH:17]=[C:16]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[C:15](=[O:25])[NH:14][NH+:13]=3)=[O:6])[CH2:40][C:39]2=[O:44])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86646547HCID 86646547, compoundHCID 86646548HCID 86646548, compound

Product 1

HCID 86646545HCID 86646545, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

OO7, 4-cyclopentyl-3-oxopiperazin-1-ium trifluoroacetate (1 eq.), TBTU (1 eq.) and N-methyl-morpholine (2.2 eq.) were stirred for 2 h in DMF. The product was purified by preparative HPLC (water/MeCN, 0.1% TFA as eluents) and desired pooled product fractions were lyophilized to afford a white powder. The powder was dissolved in DCM and washed with sat. aq. NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated to dryness to afford the product as colourless oil. 1H-NMR (300 MHz, DMSO-d6) δ: 13.52 (1H, s), 7.90 (1H, s), 7.46-7.22 (3H, m), 4.82-4.65 (1H, m), 4.15 (1H, s), 4.03 (2H, s), 3.80 (2H, s), 3.42-3.20 (3H, m), 1.80-1.40 (8H, m). MS (ES) C23H22F6N4O3 requires: 516, found: 517 (M+H)+.

Workup

  1. customThe product was purified by preparative HPLC (water/MeCN, 0.1% TFA as eluents)
  2. customto afford a white powder
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a4965a971ebf42b4867ff04fe4cc7101
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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