Dichloromethane → HCID 68650372, compound

HRID 646730Notes

Reaction equation

HRID 646730 reaction equation
[NH2:1][C:2]1[C:3]([C:51]([NH:53][CH3:54])=[O:52])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH:31]3[C:39]4[C:34](=[CH:35][C:36](CCCO[Si](C(C)(C)C)(C)C)=[CH:37][CH:38]=4)[CH2:33][CH2:32]3)S(C3C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=3)(=O)=O)[CH:9]=2)=[CH:6][N:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.C(N)(C)C.[CH2:80]1C[O:83][CH2:82][CH2:81]1>>[NH2:1][C:2]1[C:3]([C:51]([NH:53][CH3:54])=[O:52])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH:31]3[C:39]4[C:34](=[CH:35][CH:36]=[C:37]([CH2:80][CH2:81][CH2:82][OH:83])[CH:38]=4)[CH2:33][CH2:32]3)[CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 6363IsopropylamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86607843HCID 86607843, compound

Product 1

HCID 68650372HCID 68650372, compoundYield 33%

Procedure

3-Amino-6-[3-({[5-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2,3-dihydro-1H-inden-1-yl][(3,5-dinitrophenyl)sulfonyl]amino}methyl)phenyl]-N-methyl pyrazine-2-carboxamide (600 mg, 0.77 mmol) was dissolved in THF and refluxed for an hour in the presence of tetrabutylammonium fluoride in THBF. The reaction mixture was partitioned with water and extracted with ethyl acetate (10 mL×3) and dried over MgSO4. Filteration and concentration under vacuum gave tan oil, which was subjected to the solution of dichloromethane and isopropylamine. After being stirred for 30 min, the solvent was removed in vacuo and purified by flash column chromatography to give the 3-amino-6-[3-({[6-(3-hydroxypropyl)-2,3-dihydro-1H-inden-1-yl]amino}methyl)phenyl]N-methylpyrazine-2-carboxamide (110 mg, 33% yield): 1H NMR (400 MHz, CD3OD): δ 8.59 (s, 1H), 8.06 (bs, 1H), 7.91 (s, 1H), 7.52 (m, 1H), 7.40 (m, 2H), 7.11 (d, 1H), 7.08 (s, 1H), 7.03 (d, 1H), 4.32 (d, 1H), 3.66 (t, 2H), 3.02 (d, 3H), 2.99 (m, 1H), 2.81 (m, 1H), 2.69 (t, 2H), 2.44 (m, 1H), 1.90 (m, 4H), 1.32 (m, 3H), 0.82 (m, 2H); MS (EI) for C25H29N5O2: 432.23 (MH+).

Workup

  1. customThe reaction mixture was partitioned with water
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. dry with materialdried over MgSO4
  4. concentrationFilteration and concentration under vacuum
  5. customgave tan oil, which
  6. customthe solvent was removed in vacuo
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-65b273ee7a31446fb112a90982e2f01e
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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