Chlorosuccinimide → HCID 46221742, compound

HRID 1641027Notes

Reaction equation

HRID 1641027 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14](=[O:26])[C:15]([NH:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:16])=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C1C(=O)N([Cl:34])C(=O)C1>CN(C=O)C>[ClH:34].[NH2:1][C:2]1[C:10]([Cl:34])=[C:9]2[C:5]([C:6]([C:14](=[O:26])[C:15]([NH:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:16])=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[NH2:1][C:2]1[C:10]([Cl:34])=[C:9]2[C:5]([C:6]([C:14](=[O:26])[C:15]([NH:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:16])=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 46221741HCID 46221741, compound

Product 2

HCID 46221742HCID 46221742, compoundHCID 66739292HCID 66739292, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the following procedure: a solution of 2-(6-amino-1-isopropyl-1H-indol-3-yl)-2-oxo-N-(2-(piperidin-1-yl)ethyl)acetamide (150 mg, 0.42 mmol) and NCS (56 mg, 0.42 mmol) in DMF was stirred at RT overnight. The crude mixture was purified on silica gel (Biotage, 0-10% MeOH/DCM, 30 min.) to provide 2-(6-amino-7-chloro-1-isopropyl-1H-indol-3-yl)-2-oxo-N-(2-(piperidin-1-yl)ethyl)acetamide. This free amine was dissolved in DCM (2 mL) and 1M HCl in Et2O (2 mL) was added. The mixture was stirred at RT for 2 hr and additional 5 mL of Et2O was added. The light yellow solid was filtered and washed with Et2O to yield the title compound (32 mg, 18% yield): 1H NMR (400 MHz, DMSO-d6): δ 10.10 (NH+, br s, 1H), 9.04 (t, 1H), 8.79 (s, 1H), 8.07 (d, 1H), 7.09 (d, 1H), 5.56 (m, 1H), 4.18 (br s, NH2), 3.61 (q, 2H), 3.48 (d, 2H), 3.19 (d, 2H), 2.87 (m, 2H), 1.76 (m, 4H), 1.68 (d, 1H), 1.51 (d, 6H), 1.37 (m, 1H); MS (ESI) m/z: Calculated for C20H27ClN4O2: 390.2. Found: 391.2 (M+H)+.

Workup

  1. customThe crude mixture was purified on silica gel (Biotage, 0-10% MeOH/DCM, 30 min.)

Sources & evidence

ORD record
ord-b2f06a65c2dd483ca2951a82d83ed524
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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