Potassium Carbonate → HCID 58867411, compound

HRID 2426662Notes

Reaction equation

HRID 2426662 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[C:37]1[N:42]=[CH:41][CH:40]=[CH:39][N:38]=1>CN1CCCC1=O>[CH3:1][N:2]([C:37]1[N:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([N:17]3[CH2:18][CH2:19][CH:20]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=4)[CH2:21][CH2:22]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783452-BromopyrimidineHCID 58867492HCID 58867492, compound

Product 1

HCID 58867411HCID 58867411, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(R)-4-(4-Chlorophenyl)piperidine-1-carboxylic acid [4-(3-methylaminopyrrolidin-1-yl)phenyl]amide (100 mg) was reacted with potassium carbonate (100 mg) and 2-bromopyrimidine (50 mg) in N-methylpyrrolidone (3 ml) at 100° C. for 4 hours. The reaction solution was then partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated. The crude product was purified by preparative HPLC. This resulted in the product with the molecular weight of 491.04 (C27H31 ClN6O); MS (ESI): 491 (M+H+).

Workup

  1. customThe reaction solution was then partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative HPLC
  5. customThis resulted in the product with the molecular weight of 491.04 (C27H31 ClN6O)

Sources & evidence

ORD record
ord-58b991e633814ca8a19adf24beebe78a
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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