Methylamine → HCID 67433463, compound

HRID 2036660Notes

Reaction equation

HRID 2036660 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NC1N=CN=C(N[C@H]([C:53]2[N:54]=[C:55]3[CH:60]=[CH:59][CH:58]=[C:57]([C:61]([OH:63])=O)[N:56]3[C:64]=2[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)C)C=1C#N.CN>CN(C=O)C>[CH3:2][NH:3][C:61]([C:57]1[N:56]2[C:64]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)=[CH:53][N:54]=[C:55]2[CH:60]=[CH:59][CH:58]=1)=[O:63]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58459213HCID 58459213, compound

Product 1

HCID 67433463HCID 67433463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of DIEA (0.207 mL, 1.18 mmol), PyBOP (0.768 g, 1.475 mmol), and (S)-2-(1-((6-amino-5-cyanopyrimidin-4-yl)amino)ethyl)-3-phenylimidazo-[1,2-a]pyridine-5-carboxylic acid (0.236 g, 0.590 mmol) in DMF (3.93 mL) was added methanamine (2.0M in THF, 0.738 mL, 1.48 mmol). The solution was stirred at rt for 1 h then was loaded onto silica gel and purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford a solid that was repurified by reverse phase analytical HPLC (eluted with a gradient of 10-60% MeCN in water with 0.1% TFA) to afford (S)-2-(14(6-amino-5-cyanopyrimidin-4-yl)amino)-ethyl)-N-methyl-3-phenylimidazo[1,2-a]pyridine-5-carboxamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (d, J=6.65 Hz, 3H) 2.16 (d, J=4.70 Hz, 3H) 5.29 (quin, J=6.90 Hz, 1H) 6.83 (d, J=7.63 Hz, 1H) 6.93 (dd, J=6.85, 1.17 Hz, 1H) 7.18-7.46 (m, 8H) 7.74 (dd, J=9.00, 1.17 Hz, 1H) 7.94 (s, 1H) 8.51 (q, J=4.56 Hz, 1H). LC-MS (ESI) m/z 413.1 [M+H]+.

Workup

  1. custompurified by MPLC (
  2. washeluted with a gradient of 0-10% MeOH in DCM)
  3. customto afford a solid
  4. customthat was repurified by reverse phase analytical HPLC (
  5. washeluted with a gradient of 10-60% MeCN in water with 0.1% TFA)

Sources & evidence

ORD record
ord-547c5de1eaf44c80862c584619cda84d
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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