1,2-Dichloroethane → HCID 11655893, compound

HRID 1094159Notes

Reaction equation

HRID 1094159 reaction equation
[O:1]=[C:2]1[CH2:11][N:10]2[CH:12]=[C:13]([CH2:14][C:15]([O-:17])=O)[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3]1.[Na+].[NH2:19][C:20]1[CH:21]=[C:22]2[C:35](=[CH:36][CH:37]=1)[CH2:34][C:24]1([C:32]3[C:27](=[N:28][CH:29]=[CH:30][CH:31]=3)[NH:26][C:25]1=[O:33])[CH2:23]2.C(Cl)CCl.C1C=CC2N([OH:51])N=NC=2C=1>CN(C=O)C.C(O)(C(F)(F)F)=O>[O:1]=[C:2]1[C:11](=[O:51])[N:10]2[CH:12]=[C:13]([CH2:14][C:15]([NH:19][C:20]3[CH:21]=[C:22]4[C:35](=[CH:36][CH:37]=3)[CH2:34][C:24]3([C:32]5[C:27](=[N:28][CH:29]=[CH:30][CH:31]=5)[NH:26][C:25]3=[O:33])[CH2:23]4)=[O:17])[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×HCID 66636635HCID 66636635, compound2×

Product 1

HCID 11655893HCID 11655893, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of sodium (2-oxo-2,3-dihydro-1H-pyrrolo[1,2,3-de]quinoxalin-6-yl)acetate (45 mg, 0.195 mmol, described in Intermediate 26), (−)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1 H)-one (59 mg, 0.235 mmol, described in Intermediate 3), EDC (75 mg, 0.391 mmol), and HOBT (60 mg, 0.391 mmol) in DMF (12 mL) and TFA (0.1 mL) was stirred for 18 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and lyophilized to give the title compound. MS: m/z=478 (M+1). HRMS: m/z=478.1524; calculated m/z=478.1510 for C27H20N5O4.

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions

Sources & evidence

ORD record
ord-8661efbb17b44fb4b84b4f4aa62f92c4
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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