1,2-Dichloroethane → HCID 11603382, compound

HRID 1669691Notes

Reaction equation

HRID 1669691 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[C:14]2[C:21]3([CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([N+:30]([O-])=O)[CH:27]=4)[CH2:22]3)[C:20](=[O:33])[NH:19][C:15]=2[N:16]=[CH:17]N=1.[CH2:34](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:33]=[C:20]1[NH:19][C:15]2=[N:16][CH:17]=[CH:34][CH:13]=[C:14]2[C:21]21[CH2:29][C:28]1[C:23](=[CH:24][CH:25]=[C:26]([NH:30][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:27]=1)[CH2:22]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 107Benzenepropanoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59166727HCID 59166727, compound2×

Product 1

HCID 11603382HCID 11603382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-phenylpropionic acid (20 mg, 0.13 mmol), (+)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (30 mg, 0.12 mmol, described in Intermediate 5), EDC (25 mg, 0.13 mmol), HOBT (20 mg, 0.13 mmol), and N,N-diisopropylethylamine (0.023 mmol) was stirred in DMF (0.5 mL) at ambient temperature for 3 h. The crude 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. Lyophilization provided the title compound. MS: m/z=384 (M+1). HRMS: m/z=384.1725; calculated m/z=384.1707 for C24H22N3O2.

Workup

  1. customThe crude mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-69f11cb485ab45779b747fadb019655e
Source dataset
uspto-grants-2011_08
Patent number
US07989624B2

Reaction notes

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