Dichloromethane → N-(3-{8-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-4-tert-butyl-benzamide

HRID 751596Notes

Reaction equation

HRID 751596 reaction equation
[C:1]([C:5]1[CH:41]=[CH:40][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]=[C:20]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]5)=[CH:30][CH:29]=4)[C:21]4[N:22]([CH:24]=[CH:25][N:26]=4)[CH:23]=3)[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:49](OC(=O)C)(=[O:51])[CH3:50].ClCCl>O>[C:49]([N:37]1[CH2:36][CH2:35][N:34]([C:31]2[CH:32]=[CH:33][C:28]([NH:27][C:20]3[C:21]4[N:22]([CH:24]=[CH:25][N:26]=4)[CH:23]=[C:18]([C:14]4[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]5[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:41][CH:40]=5)[CH:17]=[CH:16][CH:15]=4)[N:19]=3)=[CH:29][CH:30]=2)[CH2:39][CH2:38]1)(=[O:51])[CH3:50]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 115557334-tert-Butyl-N-{3-[8-(4-piperazin-1-yl-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-benzamide

Product 1

HCID 11678734N-(3-{8-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-4-tert-butyl-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-tert-butyl-N-{3-[8-(4-piperazin-1-yl-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-benzamide (16) (0.55 mmol), triethylamine (1.1 mmol), acetic anhydride (0.60 mmol), and dichloromethane (10 mL) is stirred at room temperature for 1 hr. Water (30 mL) is added, the mixture extracted with dichloromethane (2×50 mL), the extracts washed with water (2×30 mL) and brine (1×30 mL), dried over magnesium sulfate, and concentrated in vacuo. The residue is triturated with diethyl ether and ethyl acetate to give N-(3-{8-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-4-tert-butyl-benzamide (17) as a cream solid.

Workup

  1. extractionthe mixture extracted with dichloromethane (2×50 mL)
  2. washthe extracts washed with water (2×30 mL) and brine (1×30 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is triturated with diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-e5bb405eac9d4e25b0c6ab2cb533567e
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

Loading…