1,2-Dichloroethane → HCID 178481251, compound

HRID 230008Notes

Reaction equation

HRID 230008 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([N:13]([CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=3)[C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.O.[NH:35]1[C:39]([NH2:40])=[N:38][N:37]=[N:36]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.Cl>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([N:13]([CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH:40][C:39]4[NH:38][N:37]=[N:36][N:35]=4)=[O:30])=[CH:27][CH:26]=3)[C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68834955HCID 68834955, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178481251HCID 178481251, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Example 221 Step F (0.11 mmol, 50 mg), 1H-tetraazol-5-amine monohydrate (0.23 mmol, 24 mg), HOBt (0.29 mmol, 43 mg) and EDC (0.46 mmol, 88 mg) in 1 mL of DMF was added DIEA (0.57 mmol, 100 μL). The reaction mixture was allowed to stand at ambient temperature overnight, then poured into a mixture of dilute pH 7 buffer/EtOAc, which was acidified with 2 N HCl until two clear layers formed after agitation. The organic phase was concentrated under reduced pressure and the residue was purified by reverse-phase chromatography (Condition B) and lyophilized, affording a white solid. 1H NMR (500 MHz, DMSO) δ 8.06 (d, 2H), 7.68 (d, 2H), 7.55 (m, 2H), 7.42 (d, 2H), 7.34 (m, 2H), 7.20 (d, 2H), 6.18 (m, 1H), 5.38 (s, 2H), 3.31 (s, 3H), 2.35 (m, 2H), 2.18 (m, 2H), 1.73 (m, 2H), 1.60 (m, 2H). MS (ESI): m/z 505 (M+H). HPLC A: 1.99 min.

Workup

  1. customformed after agitation
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase chromatography (Condition B)
  4. customaffording a white solid
  5. custom1.99 min.

Sources & evidence

ORD record
ord-f1eaa9c0a37a4ebf924535b16094cd35
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…