Triethylamine → HCID 22172586, compound

HRID 1823677Notes

Reaction equation

HRID 1823677 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([Cl:19])=[N:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([NH:26][CH2:27][C:28](=[O:42])[CH2:29][CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:45](CC)CC)C.[C:50]1([CH3:59])[CH:55]=[CH:54][C:53]([C:56](Cl)=[O:57])=[CH:52][CH:51]=1>C(Cl)Cl>[NH2:31][CH2:30][CH2:29][C:28]1[N:45]=[C:56]([C:53]2[CH:54]=[CH:55][C:50]([CH3:59])=[CH:51][CH:52]=2)[N:26]([CH:20]([C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:17](=[O:18])[C:16]3[C:11]([N:10]=2)=[N:12][C:13]([Cl:19])=[N:14][CH:15]=3)[CH:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH:27]=1.[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([Cl:19])=[N:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:26]([CH2:27][C:28](=[O:42])[CH2:29][CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[C:56](=[O:57])[C:53]1[CH:54]=[CH:55][C:50]([CH3:59])=[CH:51][CH:52]=1)[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 22172606HCID 22172606, compound

Product 2

HCID 22172586HCID 22172586, compoundHCID 22172632HCID 22172632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formula 402 where R1 is H; R3 is Cl; R5 is Benzyl; R6 is Isopentyl; R6′ is H; Rc is p-Tolyl; W and Y are —C═; X and Z are —N═: A solution of 2-{4-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-yl)-2-ethyl-butyl-amino]-3-oxo-butyl}-isoindole-1,3-dione (1.58 g, 2.69 mmol), triethylamine (245 mg, 2.42 mmol), and p-toluoyl chloride (374 mg, 2,42 mmol) in methylene chloride (10 mL) is stirred at room temperature for 2.0 h. The reaction is washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water and brine, and dried (Na2SO4). The filtrate is concentrated in vacuo and purified by flash chromatography (silica gel 3:2 hexanes:EtOAc as eluent) to provide the title compound, N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-yl)-2-ethyl-butyl]-N-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-butyl]-4-methyl-benzamide.

Workup

  1. washThe reaction is washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationThe filtrate is concentrated in vacuo
  4. custompurified by flash chromatography (silica gel 3:2 hexanes:EtOAc as eluent)

Sources & evidence

ORD record
ord-a1240cbc5d854e499a9d65328e74b7d6
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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