5-Chloro-1H-indole-2-carboxylic acid → HCID 11660421, compound

HRID 901986Notes

Reaction equation

HRID 901986 reaction equation
[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:12])[CH2:4][C@H:3]1[OH:13].N[C@@H]1CC2C(=C(O)C=CC=2)C[C@H]1O.[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([C:37](O)=[O:38])=[CH:31]2.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([C:37]([NH:1][C@@H:2]1[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[OH:12])[CH2:4][C@H:3]1[OH:13])=[O:38])=[CH:31]2

Participants

7

Reactant 5

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71365891(6R,7R)-6-Amino-5,6,7,8-tetrahydronaphthalene-1,7-diolHCID 71365894(6R,7R)-7-Amino-5,6,7,8-tetrahydronaphthalene-1,6-diol

Product 1

HCID 11660421HCID 11660421, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of trans 3-amino-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene and trans 3-amino-2,8-dihydroxy-1,2,3,4-tetrahydronaphthalene (278 mg, prepared in the manner disclosed in GB 1442851) was dissolved at room temperature with stirring under argon in N,N-dimethylformamide (2 mL) along with 5-chloroindole-2-carboxylic acid (315 mg), 1-hydroxy-7-azabenzotriazole (230 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (330 mg). After 3 days the reaction mixture was purified without work-up by reverse phase preparative HPLC to provide the two isomers as off-white solids, trans 3-(5-chloroindole-2-carbonylamino)-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene, Example 2 (eluted first, 130 mg) and trans 3-(5-chloroindole-2-carbonylamino)-2,8-dihydroxy-1,2,3,4-tetrahydronaphthalene, Example 3 (eluted second, 104 mg). HPLC/MS for both isomers [M+H]+, 357; [M−H]−, 355.

Workup

  1. customprepared in the manner
  2. dissolutionwas dissolved at room temperature
  3. customAfter 3 days the reaction mixture was purified without work-up by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-da5a3b036a5c417fa72f6af007806082
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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