1,2-Dichloroethane → HCID 178458179, compound

HRID 1594518Notes

Reaction equation

HRID 1594518 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13][CH3:14])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)[C:3]1=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)=[CH:28][CH:27]=1.O.[NH:38]1[C:42]([NH2:43])=[N:41][N:40]=[N:39]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13][CH3:14])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([NH:43][C:42]3[NH:41][N:40]=[N:39][N:38]=3)=[O:21])=[CH:23][CH:24]=2)[C:3]1=[N:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69417854HCID 69417854, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178458179HCID 178458179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To the title compound of Example 18, Step G (0.18 mmol, 88 mg) was added a solution of 1H-tetraazol-5-amine monohydrate (0.72 mmol, 74 mg), HOBt (0.72 mmol, 110 mg), EDC (0.72 mmol, 138 mg) and DIEA (1.08 mmol, 300 μL) in DMF (4 mL). The reaction mixture was stirred at 40° C. overnight, then concentrated under reduced pressure. The residue was taken up in 4:1 dioxane/H2O, acidified with TFA, and purified by reverse-phase chromatography (20-80% MeCN in H2O, both containing 0.1% TFA). Lyophilization afforded the title compound as a white solid. H1 NMR (500 MHz, d6-DMSO): 8.06 (d, J=6.7 Hz, 2H), 7.88 (m, 1H), 7.75 (d, J=8.5 Hz, 2H), 7.65 (dd, J=3.0, 5.0 Hz, 1H), 7.57 (d, J=4.4 Hz, 1H), 7.50-7.45 (m, 2H), 7.38 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.0 Hz, 1H), 7.05 (m, 1H), 5.55 (s, 2H), 4.04 (t, J=6.6 Hz, 2H), 3.58 (s, 1H), 3.43 (s, 3H), 3.19 (m, 2H), 1.78 (m, 2H), 1.01 (t, J=7.4 Hz, 3H). LC-MS (ESI, Method B): 1.79 min, m/z 565.0 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reverse-phase chromatography (20-80% MeCN in H2O

Sources & evidence

ORD record
ord-804eb0b4e66f4c14a08bcfb2705e0c63
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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