Methanol → HCID 59401826, compound

HRID 1916911Notes

Reaction equation

HRID 1916911 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH:14]3[CH3:18])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[NH2:19].[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].N1C=CC=CC=1.CO>C(Cl)Cl>[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH:19][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH:14]3[CH3:18])[CH2:9]2)=[CH:7][C:2]=1[CH3:1])=[O:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 98082-Fluorobenzoyl chlorideHCID 594018302-Methyl-4-(2-methyl-[1,3']bipyrrolidinyl-1'-yl)-phenylamine

Product 1

HCID 59401826HCID 59401826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Methyl-4-(2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-phenylamine (1.52 g, 5.84 mmol) was dissolved in DCM (30 mL). To this solution was transferred a solution of 2-fluorobenzoyl chloride in DCM (2 mL), followed by pyridine (7.5 mL). The solution was stirred at r.t. for 2 h when TLC (10% MeOH in DCM) and LC/MS showed that the reaction was complete. The reaction was quenched with polymer bounded diethylenetriamine (4 mmol/g, 1.5 g) and the suspension was stirred for 30 min. Then, 10 mL of DCM was added to the suspension and the suspension was filtered through a Celite pad, rinsed with DCM and 10% MeOH in DCM. The crude product was purified on a silica gel column eluted with 2%, 5% and 7.5% MeOH in DCM to obtain the title compound as a yellow solid, 1.79 g (80%). LCMS: RT=1.53 minutes, MS: 382 (M+H).

Workup

  1. customThe reaction was quenched with polymer
  2. additionThen, 10 mL of DCM was added to the suspension
  3. filtrationthe suspension was filtered through a Celite pad
  4. washrinsed with DCM and 10% MeOH in DCM
  5. customThe crude product was purified on a silica gel column
  6. washeluted with 2%, 5% and 7.5% MeOH in DCM

Sources & evidence

ORD record
ord-f8ce4f43cca046ed971eb9f275708e47
Source dataset
uspto-grants-2013_12
Patent number
US08618159B2

Reaction notes

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