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

HRID 1920050Notes

Reaction equation

HRID 1920050 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 1B 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 1.82-1.89 (m, 2 H), 1.96 (br s, 3 H), 2.22-2.28 (m, 2 H), 2.31 (t, 1 H), 3.31-3.36 (m, 2 H), 3.41-3.47 (m, 2 H), 3.60-3.66 (m, 2 H), 6.54 (dd, J=3.20, 0.76 Hz, 1 H), 7.22-7.28 (m, 1H), 7.32 (d, J=3.05 Hz, 1 H), 7.42 (d, J=8.54 Hz, 1 H), 7.60-7.62 (m, 1 H), 7.64-7.70 (m, 1 H), 8.11 ppm (d, J=1.22 Hz, 1 H); MS (ESI) m/z 310 (M+H)+.

Sources & evidence

ORD record
ord-eecd6444169f4a3d84279ad557a3deb6
Source dataset
uspto-grants-2012_05
Patent number
US08168791B2

Reaction notes

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