Diisopropylethylamine → 2-({2-Phenyl-6-[({4-[(2E)-3-phenylprop-2-enyl]piperazin-1-yl}acetyl)amino]pyrimidin-4-yl}amino)acetamide

HRID 895500Notes

Reaction equation

HRID 895500 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:32])[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23]/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:19][CH2:18]2)[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[NH2:43][CH2:44][C:45]([NH2:47])=[O:46]>>[C:8]1([C:6]2[N:7]=[C:2]([NH:43][CH2:44][C:45]([NH2:47])=[O:46])[CH:3]=[C:4]([NH:14][C:15](=[O:32])[CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH2:23]/[CH:24]=[CH:25]/[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:19][CH2:18]3)[N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723639Glycinamide hydrochlorideHCID 22353283N-(6-Chloro-2-phenylpyrimidin-4-yl)-2-{4-[(2E)-3-phenylprop-2-enyl]piperazin-1-yl}acetamide

Product 1

HCID 223534952-({2-Phenyl-6-[({4-[(2E)-3-phenylprop-2-enyl]piperazin-1-yl}acetyl)amino]pyrimidin-4-yl}amino)acetamideYield 3.9%

Conditions

Temperature
100 °C

Procedure

To a crude sample of N-(6-chloro-2-phenylpyrimidin-4-yl)-2-{4-[(2E)-3-phenylprop-2-enyl]piperazin-1-yl}acetamide (22.54) (0.75 g in 60 ml DMSO) were added glycinamide hydrochloride (1.85 g in 10 ml DMSO) and N,N-diisopropylethylamine (2.96 ml) and the mixture heated to 100° C. for 16 hrs. The solvent was then removed in vacuo and the residue purified twice by flash chromatography on silica gel using mixtures of dichloromethane and methanol (97:3, 95:5 then 93:7 v/v/v). Further purification by recrystallization from methanol furnished the title compound (32 mg over 2 steps).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified twice by flash chromatography on silica gel using mixtures of dichloromethane and methanol (97:3, 95:5
  3. customFurther purification
  4. customby recrystallization from methanol

Sources & evidence

ORD record
ord-fd88282aeb6845268ed6e7fdbcbf8255
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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