1,2-Dichloroethane → HCID 44256263, compound

HRID 2189451Notes

Reaction equation

HRID 2189451 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([C:26](O)=[O:27])[C:20]4=[N:19][N:18]=3)=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:44][C@@H:45]([CH2:48][CH3:49])[CH2:46][OH:47].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[OH:47][CH2:46][C@@H:45]([NH:44][C:26]([C:25]1[C:20]2[N:21]([C:17]([C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:12][CH:13]=3)=[N:18][N:19]=2)[CH:22]=[CH:23][CH:24]=1)=[O:27])[CH2:48][CH3:49]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 12008328895-09-2HCID 58137769HCID 58137769, compound

Product 1

HCID 44256263HCID 44256263, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-(4-(2-phenylacetamido)phenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid (59A) (14 mg, 0.038 mmol), EDC (9 mg, 0.047 mmol) and HOBt (6.4 mg, 0.047 mmol) in a mixed solvent of DMF (0.5 mL) and DCM (0.5 mL) was stirred for 5 min, and then (S)-2-aminobutan-1-ol hydrochloride salt (5.6 mg, 0.045 mmol) and triethylamine (7.6 mg, 0.075 mmol) were added. The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The crude product was purified by preparative HPLC using CH3CN/H2O/TFA solvent system to yield the title compound (8.3 mg, 50%). HPLC/MS (Method C): retention time 1.75, [M+H]+=444.5. 1H NMR (500 MHz, DMSO-d6): δ 10.50 (s, 1H), 9.58 (d, J=8.25 Hz, 1H), 8.71 (d, J=7.15 Hz, 1H), 8.14 (d, J=6.05 Hz, 1H), 7.80-7.92 (m, 4H), 7.30-7.43 (m, 4H), 7.26 (t, J=6.60 Hz, 1H), 7.19 (t, J=6.87 Hz, 1H), 3.93-4.07 (m, 1H), 3.71 (s, 2H), 3.54-3.63 (m, 1H), 3.50 (dd, J=11.0 Hz, 4.95 Hz, 1H), 1.68-1.78 (m, 1H), 1.54-1.65 (m, 1H), 0.87-1.06 (m, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cb62b7dd1d11485abaf0709217bd7e3a
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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