1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(4-tert-Butyl-3-fluorophenoxy)-N-{3-methyl-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350847Notes

Reaction equation

HRID 1350847 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][C:6]=1[F:16])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.Cl.[NH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[C:34]([CH3:43])[CH:33]=1>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[C:34]([CH3:43])[CH:33]=2)=[O:13])=[CH:7][C:6]=1[F:16])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21097504(4-tert-Butyl-3-fluorophenoxy)acetic acidHCID 21097529N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride

Product 1

HCID 115100672-(4-tert-Butyl-3-fluorophenoxy)-N-{3-methyl-4-[(methylsulfonyl)amino]benzyl}acetamideYield 17%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

(4-tert-Butyl-3-fluorophenoxy) acetic acid (339 mg, 1.5 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (518 mg, 2.7 mmol), 4-(dimethylamino)pyridine (DMAP) (55 mg, 0.45 mmol), triethylamine (0.836 ml) and N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride (451 mg, 1.8 mmol) were mixed in the same procedure described in Example 2(b) to give 105 mg (17% yield) of the title compound as a white solid.

Sources & evidence

ORD record
ord-2c8fec2a0b3f4fa280da6f04b705d83c
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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