Triethylamine → HCID 23114818, compound

HRID 748847Notes

Reaction equation

HRID 748847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:12]2[N:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][C:36](O)=[O:37])[CH:30]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.ClCCl.CCOCC.ClCCl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:12]2[N:17]=[CH:16][C:15]([CH2:18][NH:19][C:36](=[O:37])[CH2:35][C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114559[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine

Product 1

HCID 23114818HCID 23114818, compoundYield 90.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The [6-[(4-chlorophenylsulfonyl) (2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine (30 mg, 0.073 mmol) obtained in Example 351, 3-pyridylacetic acid hydrochloride (16 mg, 0.092 mmol), 4-(dimethylamino)pyridine (5 mg, 0.04 mmol) and triethylamine (0.025 ml, 0.18 mmol) were dissolved in dichloromethane (5 ml). To the resulting solution was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (17 mg, 0.089 mmol). After stirring at room temperature for 14 hours, a saturated aqueous solution (0.1 ml) of sodium bicarbonate was added to the reaction mixture. The residue obtained by concentration of the reaction mixture under reduced pressure was subjected to flash silica gel chromatography. A fraction obtained from the elution portion with dichloromethane:methanol 30:1 was concentrated under reduced pressure, whereby a white solid was obtained. The white solid was washed with ether, whereby the title compound (35 mg, 0.066 mmol, 90%) was obtained as a white powder.

Workup

  1. customThe residue obtained by concentration of the reaction mixture under reduced pressure
  2. concentrationwas concentrated under reduced pressure, whereby a white solid
  3. customwas obtained

Sources & evidence

ORD record
ord-80ffa0a6eced489493c1c20a2d5ae37d
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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