1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67287388, compound

HRID 1626516Notes

Reaction equation

HRID 1626516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23].O.ON1C2C=CC=CC=2N=N1.[CH:38]1([C:41]2[N:46]=[C:45]([O:47][CH3:48])[C:44]([CH2:49][CH2:50][NH2:51])=[CH:43][CH:42]=2)[CH2:40][CH2:39]1.Cl.C(N=C=NCCCN(C)C)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](=[O:18])[NH:51][CH2:50][CH2:49][C:44]3[C:45]([O:47][CH3:48])=[N:46][C:41]([CH:38]4[CH2:39][CH2:40]4)=[CH:42][CH:43]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidHCID 67287340HCID 67287340, compound

Product 1

HCID 67287388HCID 67287388, compoundYield 46.5%

Procedure

To a stirred solution of 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (200 mg, 0.531 mmol) and 1-hydroxybenzotriazole monohydrate (89.4 mg, 0.584 mmol) was added 2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethanamine (117 mg, 0.610 mmol) (in dimethylformamide, 3 mL). 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (112 mg, 0.584 mmol) was added and the reaction was stirred for 5 hours. The reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes to yield ethyl 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (136 mg, 0.247 mmol, 46.5% yield). MS (apci+es, positive) m/z=552.2.

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5acd9021c3ec4627b47a8cb3633a2fb0
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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