2,3-Dichlorobenzoic acid → HCID 73672103, compound

HRID 514924Notes

Reaction equation

HRID 514924 reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][N:5]([CH:8]([C:11]2[CH:12]=[N:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:9][NH2:10])[CH2:4][CH2:3]1.[Cl:19][C:20]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:19][C:20]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:10][CH2:9][CH:8]([N:5]1[CH2:6][CH2:7][C:2]([F:1])([F:18])[CH2:3][CH2:4]1)[C:11]1[CH:12]=[N:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:23]

Participants

7

Reactant 5

HCID 57652,3-Dichlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86716019HCID 86716019, compound

Product 1

HCID 73672103HCID 73672103, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4,4-difluoro-piperidin-1-yl)-2-(6-fluoro-pyridin-3-yl)-ethylamine (100 mg, 0.38 mmol), 2,3-dichlorobenzoic acid (51 mg, 0.28 mmol), HOBT (57 mg, 0.42 mmol), EDC.HCl (81 mg, 0.42 mmol) and DIPEA (108 mg, 0.84 mmol) in DMF (4 mL) was stirred at room temperature overnight. The mixture was purified by preparative HPLC directly to yield the title compound (43 mg, yield: 30%)

Workup

  1. customThe mixture was purified by preparative HPLC directly

Sources & evidence

ORD record
ord-db17ad4ac7da41dd988408a36f7cb635
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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