1,2-Dichloroethane → HCID 178433410, compound

HRID 526521Notes

Reaction equation

HRID 526521 reaction equation
C(Cl)CCl.C1C=[CH:7][C:8]2[N:13](O)N=N[C:9]=2[CH:10]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][N:30]=3)[C:27]=2[OH:28])=[CH:19][CH:18]=1)#[N:16].Cl.CC1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([NH:13][C:8]4([CH3:7])[CH2:10][CH2:9]4)=[O:35])=[CH:31][N:30]=3)[C:27]=2[OH:28])=[CH:21][CH:22]=1)#[N:16]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12953687(1-Methylcyclopropyl)amine hydrochlorideHCID 178509615HCID 178509615, compound

Product 1

HCID 178433410HCID 178433410, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Combined EDC (56.3 mg, 0.294 mmol), HOBT (39.7 mg, 0.294 mmol) and 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (45 mg, 0.147 mmol) in DMF (0.8 mL) then added 1-methylcyclopropanamine hydrochloride (47.4 mg, 0.441 mmol) and Hunig's base (0.180 mL, 1.028 mmol) and stirred at 20° C. for 16 h. The reaction mixture was diluted with 100 uL DMSO and purified by prep HPLC (ACN/water with formic acid) to give the title compound (27 mg, 51.1% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.60-0.68 (m, 2H) 0.73-0.81 (m, 2H) 1.40 (s, 3H) 7.75 (d, J=8.6 Hz, 2H) 8.06-8.16 (m, 2H) 8.35 (dd, J=8.6, 2.3 Hz, 1H) 8.46 (d, J=8.8 Hz, 1H) 8.54 (s, 1H) 8.82-8.90 (m, 2H) 13.53 (br. s., 1H). MS m/z 360 [M+H]+.

Workup

  1. custompurified by prep HPLC (ACN/water with formic acid)

Sources & evidence

ORD record
ord-774d601518e4466b9c6435e0015ddb94
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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