1,2-Dichloroethane → HCID 86729372, compound

HRID 521210Notes

Reaction equation

HRID 521210 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([N:17]2[CH:21]=[C:20]([C:22](O)=[O:23])[C:19]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:18]2)([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:33][N:34](C(C)C)C(C)C.CN.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:15]([CH2:14][C:11]1([N:17]2[CH:21]=[C:20]([C:22](=[O:23])[NH:34][CH3:33])[C:19]([NH:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:18]2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]1)#[N:16]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86729371HCID 86729371, compound

Product 1

HCID 86729372HCID 86729372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(tert-butoxycarbonyl)-4-(cyanomethyl)piperidin-4-yl]-3-(phenylamino)-1H-pyrazole-4-carboxylic acid (25 mg, 0.059 mmol) in DCM (0.6 mL) was added DIPEA (0.030 mL, 0.18 mmol), methylamine (0.040 mL, 0.082 mmol, 2.0 M in THF), HOBT (13 mg, 0.082 mmol), and EDC (16 mg, 0.082 mmol). The resulting mixture was maintained at ambient temperature for 18 hours, then purified directly by MPLC on silica gel (using a gradient elution of 0-10% MeOH/DCM) to afford the title compound.

Workup

  1. custompurified directly by MPLC on silica gel (
  2. washa gradient elution of 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-6f1f75c544c64e00870fcc406f71c28f
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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