N-(phenylsulfonyl)sarcosine → HCID 67368278, compound

HRID 553485Notes

Reaction equation

HRID 553485 reaction equation
[C:1]1([S:7]([N:10]([CH2:12][C:13]([OH:15])=O)[CH3:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([N:52]3[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]3)=[N:48][CH:49]=[CH:50][N:51]=2)=[CH:42][CH:41]=1>ClCCl>[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([N:52]3[CH2:53][CH2:54][N:55]([C:13](=[O:15])[CH2:12][N:10]([CH3:11])[S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:8])=[O:9])[CH2:56][CH2:57]3)=[N:48][CH:49]=[CH:50][N:51]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 4379N-(phenylsulfonyl)sarcosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazine

Product 1

HCID 67368278HCID 67368278, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (benzenesulfonyl-methyl-amino)-acetic acid (0.150 g, 0.654 mmol) in dichloromethane (5 mL). Add 1-hydroxybenzotriazole hydrate (0.081 g, 0.595 mmol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.114 g, 0.595 mmol). Add 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.154 g, 0.595 mmol) and stir at ambient temperature for 18 hr. Add dichloromethane and water and separate layers. Extract the aqueous layer three times with dichloromethane. Dry the combined organic layers over magnesium sulfate, filter and concentrate under reduced pressure to give residue. Purify the residue by chromatography on silica gel eluting with 50-100% ethylacetate/hexanes to give the title preparation (193 mg, 69% yield). MS (ES+) m/z: 470 (M+H)+.

Workup

  1. customAdd dichloromethane and water and separate layers
  2. extractionExtract the aqueous layer three times with dichloromethane
  3. dry with materialDry the combined organic layers over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give residue
  7. customPurify the residue by chromatography on silica gel eluting with 50-100% ethylacetate/hexanes
  8. customto give the title
  9. custompreparation (193 mg, 69% yield)

Sources & evidence

ORD record
ord-49404a67aa1a47618c530f1dcf41610e
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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