1,2-Dichloroethane → HCID 12096227, compound

HRID 398385Notes

Reaction equation

HRID 398385 reaction equation
[OH:1][C:2]([CH3:28])([CH3:27])[CH2:3][N:4]1[CH2:8][C@H:7]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][C:17]([OH:19])=O)[C:11](=[O:20])[CH:10]=2)[C@H:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5]1.Cl.Cl.[NH2:31][CH2:32][C:33]1[CH:34]=[C:35]2[C:39](=[N:40][CH:41]=1)[NH:38][CH:37]=[C:36]2[F:42].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[OH:1][C:2]([CH3:27])([CH3:28])[CH2:3][N:4]1[CH2:8][C@H:7]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][C:17]([NH:31][CH2:32][C:33]3[CH:34]=[C:35]4[C:39](=[N:40][CH:41]=3)[NH:38][CH:37]=[C:36]4[F:42])=[O:19])[C:11](=[O:20])[CH:10]=2)[C@H:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12096228HCID 12096228, compoundHCID 86759147HCID 86759147, compound

Product 1

HCID 12096227HCID 12096227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(1-(2-hydroxy-2-methylpropyl)-cis-3-phenylpyrrolidin-4-yl)-6-methyl-1-carboxymethyl-2-pyridinone from step 8 above (0.23 mmol), 5-aminomethyl-3-fluoro-7-azaindole bis hydrochloride (55 mg, 0.23 mmol), HOBT (35 mg, 0.23 mmol) and DIEA (0.12 mL, 0.69 mmol) in DMF (2 mL) was added EDC (134 mg, 0.46 mmol). The resulting solution was stirred at ambient temperature for 18 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography using a gradient elution of 96:4 to 92:8 CH2Cl2:MeOH as eluant to give the title compound as an amorphous solid (0.1 g, TLC Rf=0.4, 92:8 CH2Cl2:MeOH; HPLC RT=4.71 min, method A).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography
  3. washa gradient elution of 96:4 to 92:8 CH2Cl2

Sources & evidence

ORD record
ord-b92c08bc966847ca92c44782c41d3e73
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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