1,2-Dichloroethane → HCID 11294495, compound

HRID 229985Notes

Reaction equation

HRID 229985 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)[CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]1.C([O:35][C:36](=[O:40])[CH2:37][CH2:38][NH2:39])(C)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:39][CH2:38][CH2:37][C:36]([OH:35])=[O:40])=[O:27])=[CH:24][CH:23]=1)[CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([CH3:20])([CH3:18])[CH3:19])[CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4192171tert-Butyl 3-aminopropanoateHCID 688356554-{[1h-Benzimidazol-2-yl(4-tert-butylcyclohexyl)amino]methyl}benzoic acid

Product 1

HCID 11294495HCID 11294495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 1 Step D (0.1 mmol, 41 mg), the hydrochloride salt of β-alanine tert-butyl ester (0.15 mmol, 27 mg), HOBt (0.25 mmol, 38 mg) and EDC (0.4 mmol, 77 mg) in 1 mL of DMF was added DIEA (0.5 mmol, 90 μL). The reaction mixture was allowed to stand at ambient temperature overnight, then partitioned into EtOAc/H2O. The aqueous phase was washed with EtOAc, and the combined organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The residue was treated with 3 mL of 2:30:68H2O/TFA/DCM for 1 hr and the solution was concentrated under reduced pressure. Purification by reverse-phase chromatography (Condition A), followed by lyophilization, afforded the product as a white solid. MS (ESI): m/z 477 (M+H). HPLC A: 1.70 min.

Workup

  1. custompartitioned into EtOAc/H2O
  2. washThe aqueous phase was washed with EtOAc
  3. dry with materialthe combined organic phase was dried with MgSO4
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was treated with 3 mL of 2:30:68H2O/TFA/DCM for 1 hr
  6. concentrationthe solution was concentrated under reduced pressure
  7. customPurification by reverse-phase chromatography (Condition A),

Sources & evidence

ORD record
ord-701a0e8238d64194a6f512b591dca443
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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