1H-Indole-5-Carboxylic Acid → HCID 67501352, compound

HRID 1920051Notes

Reaction equation

HRID 1920051 reaction equation
[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C@@H:4]3[CH2:11][NH2:12])[CH2:2]1)[CH2:8]2.[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22](O)=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>N1C=CC=CC=1>[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C@@H:4]3[CH2:11][NH:12][C:22]([C:18]3[CH:17]=[C:16]4[C:21](=[CH:20][CH:19]=3)[NH:13][CH:14]=[CH:15]4)=[O:23])[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 742801H-Indole-5-Carboxylic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189378471-Azatricyclo[3.3.1.13,7]decane-4-methanamine

Product 1

HCID 67501352HCID 67501352, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product of Example 2B was reacted with indole-5-carboxylic acid, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole and 4-di(methylamino)pyridine in pyridine as described in Example 3 to afford the title compound: 1H NMR (methanol-d4, 500 MHz) δ 1.91 (br s, 2 H), 1.94-2.01 (m, 3 H), 2.11-2.18 (m, 2 H), 2.24 (t, J=7.93 Hz, 1 H), 3.16-3.21 (m, 2 H), 3.59-3.65 (m, 4 H), 6.54 (dd, J=3.05, 0.92 Hz, 1 H), 7.22-7.28 (m, 1 H), 7.32 (d, J=3.05 Hz, 1 H), 7.41-7.44 (m, 1 H), 7.60 (dd, J=8.54, 1.83 Hz, 1 H), 7.63-7.70 (m, 1 H), 8.10 ppm (d, J=1.83 Hz, 1 H); MS (ESI) m/z 310 (M+H)+.

Sources & evidence

ORD record
ord-d0a5102691c34cf1976680780cc3c8ce
Source dataset
uspto-grants-2012_05
Patent number
US08168791B2

Reaction notes

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