Methylamine → HCID 53482872, compound

HRID 2036646Notes

Reaction equation

HRID 2036646 reaction equation
[NH2:1][C:2]1[C:3]([C:30]#[N:31])=[C:4]([NH:8][C@H:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([OH:21])=O)[N:14]3[C:22]=2[C:23]2[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=2)[CH3:10])C=CC=1.F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:43]2C=CC=CC=2N=N1.CC[N:67]([CH:71](C)C)C(C)C.C[NH2:75]>CN(C=O)C>[NH2:75][C:2]1[N:1]=[CH:43][N:39]=[C:4]([NH:8][C@H:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:67][CH3:71])=[O:21])[N:14]3[C:22]=2[C:23]2[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=2)[CH3:10])[C:3]=1[C:30]#[N:31]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58459378HCID 58459378, compound

Product 1

HCID 53482872HCID 53482872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(1-((3-amino-2-cyanophenyl)amino)ethyl)-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridine-5-carboxylic acid (0.058 g, 0.139 mmol) in DMF (0.93 mL) was added benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (181 mg, 0.348 mmol) followed by DIEA (0.049 mL, 0.278 mmol) and methylamine (2.0M solution in THF, 0.174 mL, 0.348 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 0-8% MeOH in DCM) to afford a light yellow solid. Repurified by MPLC (eluted with a gradient of 0-90% (1:10:90 NH4OH:MeOH:DCM solution) in DCM) to afford 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-3-(5-fluoro-3-pyridinyl)-N-methylimidazo-[1,2-a]pyridine-5-carboxamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (br. s., 3H) 2.28 (d, J=4.70 Hz, 3H) 5.35 (quin, J=6.94 Hz, 1H) 7.00 (dd, J=6.75, 0.88 Hz, 1H) 7.08 (d, J=7.43 Hz, 1H) 7.22 (br. s., 2H) 7.39 (dd, J=9.00, 6.85 Hz, 1H) 7.67 (br. s., 1H) 7.78 (dd, J=9.10, 0.88 Hz, 1H) 7.87 (s, 1H) 8.31 (br. s., 1H) 8.57 (d, J=2.74 Hz, 1H) 8.73 (q, J=4.30 Hz, 1H). LC-MS (ESI) m/z 432.0 [M+H]+.

Workup

  1. custompurified by MPLC (
  2. washeluted with a gradient of 0-8% MeOH in DCM)
  3. customto afford a light yellow solid
  4. customRepurified by MPLC (
  5. washeluted with a gradient of 0-90% (1:10:90 NH4OH:MeOH:DCM solution) in DCM)

Sources & evidence

ORD record
ord-1112c26314604542939d0c856380edc6
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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