3-(Methoxycarbonyl)benzoic acid → Methyl 3-(2-(2-phenylpyrimidin-5-ylcarbamoyl)-4-(piperidin-1-yl)-phenylcarbamoyl)benzoate

HRID 926797Notes

Reaction equation

HRID 926797 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][CH:12]=1)=[O:5].[CH3:29][O:30][C:31]([C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](O)=[O:37])=[O:32].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:13]1([C:10]2[N:11]=[CH:12][C:7]([NH:6][C:4]([C:3]3[CH:19]=[C:20]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:21]=[CH:22][C:2]=3[NH:1][C:36]([C:35]3[CH:34]=[C:33]([CH:41]=[CH:40][CH:39]=3)[C:31]([O:30][CH3:29])=[O:32])=[O:37])=[O:5])=[CH:8][N:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665870272-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide

Product 1

HCID 66586957Methyl 3-(2-(2-phenylpyrimidin-5-ylcarbamoyl)-4-(piperidin-1-yl)-phenylcarbamoyl)benzoateYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide (2 g, 3.75 mmol, 1.00 equiv, 70%) in dichloromethane (30 mL) was added 3-(methoxycarbonyl)benzoic acid (1160 mg, 6.12 mmol, 1.20 equiv, 95%), EDC.HCl (2040 mg, 10.20 mmol, 2.00 equiv, 95%), and 4-dimethylaminopyridine (660 mg, 5.14 mmol, 1.00 equiv, 95%) and the resulting solution was stirred for 3 h at 25° C. in an oil bath. The mixture was concentrated under vacuum, diluted with 100 mL of ethyl acetate, washed with 1×100 mL of brine and then the organic layer was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (2:1) to afford 1200 mg (60%) of product as a green to yellow solid.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additiondiluted with 100 mL of ethyl acetate
  3. washwashed with 1×100 mL of brine
  4. concentrationthe organic layer was concentrated under vacuum
  5. washeluted with petroleum ether/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-92dad38ad03c4b4f9c83a2fd1a8c3986
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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