1,3-Benzodioxole-5-ethanamine → HCID 67081552, compound

HRID 1048097Notes

Reaction equation

HRID 1048097 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH2:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)[O:20][CH2:19][CH2:18][CH:17]2[C:34]([O:36][CH2:37][CH3:38])=[O:35].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][C:29]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]4[CH:22]=[C:21]5[C:16]([CH:17]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:18][CH2:19][O:20]5)=[CH:15][C:14]=4[Cl:13])=[CH:33][CH:32]=3)=[O:30])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 738741,3-Benzodioxole-5-ethanamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Product 1

HCID 67081552HCID 67081552, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Benzo[d][1,3]dioxol-5-yl)ethanamine (32.9 mg, 0.199 mmol) in DMF (0.1 M) was treated sequentially with 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation 1) (1327 μL, 0.133 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (30.5 mg, 0.159 mmol), and 1-hydroxy-7-azabenzotriazole (5.42 mg, 0.0398 mmol) at ambient temperature. After 16 hours, the reaction was applied directly to a silica gel column and eluted with a gradient (20% to 80%) of ethyl acetate-hexanes to provide the title compound (65 mg, 0.124 mmol, 93.5% yield) as a white solid.

Workup

  1. washeluted with a gradient (20% to 80%) of ethyl acetate-hexanes

Sources & evidence

ORD record
ord-d2fd54676eb74399a72586f0c6f644c2
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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