1-Methylpiperazine → HCID 53482416, compound

HRID 2036670Notes

Reaction equation

HRID 2036670 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C@H:16]([C:18]2[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26](O)=[O:27])[N:21]3[C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:17])[C:10]=1[C:36]#[N:37].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:8][C:9]1[C:10]([C:36]#[N:37])=[C:11]([NH:15][C@H:16]([C:18]2[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:27])[N:21]3[C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:17])[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58459213HCID 58459213, compound

Product 1

HCID 53482416HCID 53482416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-methylpiperazine (0.040 mL, 0.356 mmol), (S)-2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-3-phenylimidazo[1,2-a]pyridine-5-carboxylic acid (0.071 g, 0.178 mmol), PyBOP (0.185 g, 0.356 mmol) and DIEA (0.062 mL, 0.356 mmol) in DMF (1.78 mL) was stirred at rt for 1 h. The solution was loaded onto silica gel and purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford an off-white solid that was repurified by MPLC (eluted with a gradient of 0-80% (1:10:90 NH4OH:MeOH:DCM) solution in DCM) to afford 4-amino-6-(((1S)-1-(5-((4-methyl-1-piperazinyl)carbonyl)-3-phenylimidazo[1,2-a]pyridin-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43 (dd, J=14.18, 6.75 Hz, 3H) 1.88-2.01 (m, 1H) 2.03-2.10 (m, 1H) 2.12-2.44 (m, 6H) 3.00-3.14 (m, 1H) 3.22 (m, J=9.19 Hz, 1H) 3.40 (d, J=4.30 Hz, 1H) 5.13-5.34 (m, 1H) 6.75-6.98 (m, 2H) 7.16-7.53 (m, 8H) 7.75 (m, J=9.00, 5.09 Hz, 1H) 7.94 (d, J=6.85 Hz, 1H). LC-MS (ESI) m/z 482.1 [M+H]+.

Workup

  1. custompurified by MPLC (
  2. washeluted with a gradient of 0-10% MeOH in DCM)
  3. customto afford an off-white solid
  4. customthat was repurified by MPLC (
  5. washeluted with a gradient of 0-80% (1:10:90 NH4OH:MeOH:DCM) solution in DCM)

Sources & evidence

ORD record
ord-d53ad563393f467394d94c5c04204931
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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