1,2-Dichloroethane → HCID 66562026, compound

HRID 1850802Notes

Reaction equation

HRID 1850802 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:21]3[N:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][C:22]=3[CH3:31])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[F:32][CH:33]1[CH2:36][NH:35][CH2:34]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[F:32][CH:33]1[CH2:36][N:35]([C:28](=[O:29])[CH2:27][C:24]2[CH:23]=[C:22]([CH3:31])[C:21]([O:20][CH2:19][CH2:18][C@@H:16]3[CH2:17][C@@H:15]3[CH:12]3[CH2:13][CH2:14][N:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:2])[CH3:3])[N:8]=4)[CH2:10][CH2:11]3)=[N:26][CH:25]=2)[CH2:34]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 36035423-FluoroazetidineHCID 70856015HCID 70856015, compound

Product 1

HCID 66562026HCID 66562026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of [6-(2-{(1S,2R)-2-[1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl]cyclopropyl}ethoxy)-5-methylpyridin-3-yl]acetic acid (25 mg, 0.058 mM), 3-floroazetidine (8.7 mg, 0.116 mmol), EDC (17 mg, 0.087 mmol), HOBt (13 mg. 0.087 mmol) and triethyl amine (33 μL, 0.232 mmol) in 2 mL of DCM was stirred for 16 hrs at room temperature. The volatiles were then removed in vacuo and the residue was dissolved in CH3CN and water (1/1, 1.5 ml) and submitted to the Rahway High Throughput Purification Group to be purified. The HTP group used an HP mass-directed LC eluting with a gradient of 20-80% acetonitrile in water with 0.05% formic acid buffer to purify the compound. The desired product was obtained with 97.5% purity measured via Gilson HPLC analytical analysis. LCMS (ESI) m/z 486 [M+H]+. GPR119 Human EC50: 8 nM

Workup

  1. customThe volatiles were then removed in vacuo
  2. dissolutionthe residue was dissolved in CH3CN
  3. customwater (1/1, 1.5 ml) and submitted to the Rahway High Throughput Purification Group
  4. customto be purified
  5. washeluting with a gradient of 20-80% acetonitrile in water with 0.05% formic acid buffer
  6. customto purify the compound

Sources & evidence

ORD record
ord-de18a018f7c04f7ea3f0176b837c6b39
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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