3-(Dimethylamino)pyrrolidine → 1-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}-N,N-dimethylpyrrolidin-3-amine

HRID 1520058Notes

Reaction equation

HRID 1520058 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)[CH:14]=2)=[N:2]1.[CH3:24][N:25]([CH3:31])[CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([N:28]4[CH2:29][CH2:30][CH:26]([N:25]([CH3:31])[CH3:24])[CH2:27]4)=[O:20])=[CH:22][CH:23]=3)[CH:14]=2)=[N:2]1

Participants

3

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 679811434-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

Product 1

HCID 679845941-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}-N,N-dimethylpyrrolidin-3-amine

Procedure

The title compound was obtained following procedure described for example 26, but starting from 4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid (100 mg; 0.33 mmol; 1.0 eq.) and 3-dimethylamino pyrrolidine (56 mg, 0.49, 1.5 eq.). Purification by flash chomatography on silica (DCM:MeOH:NH4OH, gradient from 100:0:0 to 90:10:0.1) afforded the title compound as a yellow powder. 1H NMR (300 Mz, DMSO-d6) δ 13.37 (s, 1H), 9.39 (s, 1H), 8.36 (d, J=8.2 Hz, 1H), 8.13 (d, J=8.3 Hz, 2H), 7.83-7.72 (m, 2H), 7.61 (d, J=8.4 Hz, 1H), 7.53-7.36 (m, 1H), 7.33-7.19 (m, 1H), 3.77-3.18 (m, 5H), 2.78-2.60 (m, 1H), 2.24-1.92 (m, 6H), 1.82-1.69 (m, 1H). HPLC (Condition A): Rt 2.20 min (purity 90.1%). MS (ESI+): 402.3, MS (ESI−): 400.3.

Workup

  1. customPurification by flash chomatography on silica (DCM:MeOH:NH4OH, gradient from 100:0:0 to 90:10:0.1)

Sources & evidence

ORD record
ord-4b2480baa0994a2f85a6c1756d0317ca
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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