N-Methylpyridine-4-methylamine → (S)-2-{4-[4-(1-Acetylamino-ethyl)-phenyl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid methyl-pyridin-4-ylmethyl-amide

HRID 1470759Notes

Reaction equation

HRID 1470759 reaction equation
[C:1]([NH:4][C@H:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][N:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:61][NH:62][CH2:63][C:64]1[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=1>CN(C=O)C>[CH3:61][N:62]([CH2:63][C:64]1[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=1)[C:25]([C:22]1[CH:21]=[N:20][C:19]([N:16]2[CH2:17][CH2:18][CH:13]([C:10]3[CH:9]=[CH:8][C:7]([C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:6])=[CH:12][CH:11]=3)[CH2:14][CH2:15]2)=[N:24][CH:23]=1)=[O:27]

Participants

6

Reactant 4

HCID 81436N-Methylpyridine-4-methylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67125410(S)-2-{4-[4-(1-Acetylamino-ethyl)-phenyl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid

Product 1

HCID 67970548(S)-2-{4-[4-(1-Acetylamino-ethyl)-phenyl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid methyl-pyridin-4-ylmethyl-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 36.8 mg (0.1 mmol) (S)-2-{4-[4-(1-acetylamino-ethyl)-phenyl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid (XVII.1) and 51 μL (0.3 mmol) DIPEA in 2 mL DMF is added 38.0 mg (0.1 mmol) HATU and the mixture is stirred for 15 min at rt. Subsequent the mixture is added to 12.2 mg (0.1 mmol) methylpyridin-4-ylmethylamine and stirring is continued for 12 h. The solvent is removed in vacuo and the residue is purified using reversed phase column chromatography (water+0.1% NH4OH/MeOH) and the corresponding fractions are concentrated to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued for 12 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified
  5. concentrationthe corresponding fractions are concentrated

Sources & evidence

ORD record
ord-a4bbc9ad9dbd4e39b5b9219a2f5b706b
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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