Triethylamine → N-{4-[4-(4,6-dimethyl-pyridin-2-yl)-[1,4]diazepan-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide

HRID 37880Notes

Reaction equation

HRID 37880 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:3]=1.[O:23]=[C:24]([C:28]1[N:36]2[C:31]([CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:30][C:29]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:25](Cl)=[O:26].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:25](=[O:26])[C:24](=[O:23])[C:28]4[N:36]5[C:31]([CH2:32][CH2:33][CH2:34][CH2:35]5)=[CH:30][C:29]=4[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[CH:20][CH:21]=3)[CH2:11][CH2:10]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66851256HCID 66851256, compoundHCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

Product 1

HCID 25122031N-{4-[4-(4,6-dimethyl-pyridin-2-yl)-[1,4]diazepan-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(4,6-dimethyl-pyridin-2-yl)-[1,4]diazepan-1-yl]-phenyl amine (prepared as described in Reference Example 90, 800 mg, 2.70 mmol) in DCM (30 mL) was added oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in Reference Example 21, 930 mg, 3.24 mmol) and triethylamine (0.75 mL, 5.4 mmol). The mixture was stirred for 2 h at room temperature then concentrated in vacuo to give a residue which was purified by flash chromatography on silica gel (60-120 mesh) eluting with 30% ethyl acetate/n-hexane to afford N-{4-[4-(4,6-dimethyl-pyridin-2-yl)-[1,4]diazepan-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (500 mg, 35%) as a yellow solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give a residue which
  3. customwas purified by flash chromatography on silica gel (60-120 mesh)
  4. washeluting with 30% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-4ccb5d953d75460ab7c0ed32d46ad036
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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