Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-(4-morpholin-4-yl-piperidin-1-yl)-2-oxo-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359753Notes

Reaction equation

HRID 1359753 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:62]1[CH2:67][CH2:66][CH:65]([N:68]2[CH2:73][CH2:72][O:71][CH2:70][CH2:69]2)[CH2:64][CH2:63]1.[Li+].[Cl-]>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([N:62]2[CH2:67][CH2:66][CH:65]([N:68]3[CH2:73][CH2:72][O:71][CH2:70][CH2:69]3)[CH2:64][CH2:63]2)=[O:32])[C:25]=1[CH3:34])(=[O:11])=[O:12]

Participants

7

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 433294Lithium ChlorideHCID 7957244-MorpholinopiperidineHCID 59077497HCID 59077497, compound

Product 1

HCID 590777345-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-(4-morpholin-4-yl-piperidin-1-yl)-2-oxo-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (1 eq.) and BOP (1.25 eq.) were suspended in DMF (5 mL) at rt and TEA (2.4 eq.) was added. After 15 mins, to the homogenous reaction mixture was added 4-piperidin-4-yl-morpholine (1.25 eq.) all at once. After stirring for 2 days, the reaction was added to a mixture of chloroform-isopropanol (5:1) and 5% aq. LiCl. The organic layer was separated, washed with 5% aq. LiCl (2×), 1 M aq. NaOH (3×), brine, dried and concentrated. The residue was purified to give the titled compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with 5% aq. LiCl (2×), 1 M aq. NaOH (3×), brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-bf3493ac74a34398ba97a224afa7cc62
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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