Carbonate Ion → HCID 68917833, compound

HRID 1191287Notes

Reaction equation

HRID 1191287 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH:9]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:14]=[CH:13][N:12]=2)[CH2:8][CH2:7][CH2:6][N:5]1[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.N=C=N.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([C:46](O)=[O:47])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].OC1C2N=NNC=2C=CC=1.C(=O)([O-])[O-]>ClCCl.CN(C)C=O>[N:17]1([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][CH:9]3[CH2:8][CH2:7][CH2:6][N:5]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH:4]3[CH2:3][CH2:2][NH:1][C:46]([CH:43]3[CH2:44][CH2:45][N:40]([C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:39])[CH2:41][CH2:42]3)=[O:47])[N:16]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 19660Carbonate IonHCID 160435CarbodiimideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 11848560HCID 11848560, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 68917833HCID 68917833, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

N-[(2RS,3SR)-2-(2-aminoethyl)-1-cyclohexylpiperidin-3-yl]-4-azepan-1-ylpyrimidin-2-amine (63 mg) was dissolved in dichloromethane (3 mL), PS-carbodiimide (327 mg) was added and then 0.5 M of a solution (0.47 mL) of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid in dimethylformamide:dichloromethane=1:1 and 0.5 M of a mixture solution (0.53 mL) of hydroxybenzotriazole in dimethylformamide:dichloromethane=1:1 were added and stirred at room temperature for overnight. MP-carbonate (271 mg) was added into the reaction solution, stirred for 1 hour and then filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=90:10) to obtain the title compound (81 mg) having the following physical properties.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=90:10)

Sources & evidence

ORD record
ord-5d29c971ae884260b704f89255914fc8
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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