Iodoethane → HCID 22346795, compound

HRID 897854Notes

Reaction equation

HRID 897854 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[NH:23][C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])=[C:15]([O:31][CH3:32])[CH:14]=3)[C:5]=12.[CH2:39](I)[CH3:40].F[C:43](F)(F)[C:44]([OH:46])=[O:45]>CN(C)C=O>[C:44]([O-:46])(=[O:45])[CH3:43].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:33]3[CH2:34][CH2:35][NH2+:36][CH2:37][CH2:38]3)[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[N:23]([CH2:39][CH3:40])[C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:21])=[C:15]([O:31][CH3:32])[CH:14]=3)[C:5]=12

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 20817342HCID 20817342, compound

Product 1

HCID 22346795HCID 22346795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride, 60% suspension in mineral oil (0.006 g, 0.15 mmol) was added into the solution of N2-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1H-2-indolecarboxamide (0.08 g, 0.14 mmol) in N,N-dimethylforamide (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and at ambient temperature for 20 minutes. A solution of ethyl iodide (0.02 g, 0.14 mmol) in N,N-dimethylforamide (0.5 mL) was added in and the mixture was stirred at ambient temperature overnight. Ethyl iodide (0.01 g, 0.07 mmol) was added in and the mixture was stirred at ambient temperature overnight. Trifluoroacetic acid (3 mL) was added and the mixture was stirred at ambient temperature for 24 hours. The solvents and excess reagents were evaporated under reduced pressure and the residue was purified by preparative HPLC to yield 4-[4-amino-3-(4-{[(1-ethyl-1H-2-indolyl)carbonyl]amino}-3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]hexahydropyridinium acetate (0.05 g, 0.09 mmol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 8.27 (s, 1H), 8.14 (d, 1H), 7.71(d, 1H), 7.61 (d, 1H), 7.34 (s, 2H), 7.31 (t, 2H), 7.15 (t, 1H), 4.96 (m, 1H), 4.62 (q, 2H), 3.96 (s, 3H), 3.00 (m, 2H), 2.28 (m, 2H), 2.03 (m, 2H), 1.91 (s, 3H), 1.33 (t, 3H); MS: MH+ 511.

Workup

  1. stirringwas stirred at ambient temperature overnight
  2. stirringwas stirred at ambient temperature overnight
  3. stirringthe mixture was stirred at ambient temperature for 24 hours
  4. customThe solvents and excess reagents were evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bf410fea9e6a4360a1c2110edb45d25d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…