1,2-Dichloroethane → HCID 59525834, compound

HRID 386049Notes

Reaction equation

HRID 386049 reaction equation
[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:11][C:10]=2[F:20])[S:6][C:5]=1[NH:21][C:22]1[N:27]=[C:26]([CH2:28][N:29]2[C:33]([C:34]([O-:36])=O)=[CH:32][N:31]=[N:30]2)[CH:25]=[CH:24][CH:23]=1)=[O:3].[K+].C1C=CC2N(O)N=[N:44][C:42]=2C=1.C(Cl)CCl.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:10]([F:20])=[CH:11][C:12]([C:16]([OH:19])([CH3:17])[CH3:18])=[CH:13][C:14]=2[F:15])[S:6][C:5]=1[NH:21][C:22]1[N:27]=[C:26]([CH2:28][N:29]2[C:33]([C:34]([NH:44][CH3:42])=[O:36])=[CH:32][N:31]=[N:30]2)[CH:25]=[CH:24][CH:23]=1)=[O:3]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 68671465HCID 68671465, compound

Product 1

HCID 59525834HCID 59525834, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium 1-{[6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}-1H-1,2,3-triazole-5-carboxylate (131 mg, 0.24 mmol), HOBT (72.6 mg, 0.47 mmol), EDC (91 mg, 0.47 mmol), and methylamine hydrochloride (48 mg, 0.71 mmol) were combined in DMF (5.0 mL), and DIEA (124 μL, 0.71 mmol) was added. The reaction was stirred at room temperature overnight. The solution was diluted with water. The precipitate was collected by filtration, washed with water and CH2Cl2, and dried to provide the title compound as an off-white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and CH2Cl2
  3. customdried

Sources & evidence

ORD record
ord-7bec52bd80cb4e1c83fa157a10bfec7c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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