Triethylamine → HCID 42599839, compound

HRID 908490Notes

Reaction equation

HRID 908490 reaction equation
Cl[C:2](=[O:8])[CH2:3][O:4]C(=O)C.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[C:18]1[C:19]([NH2:38])=[N:20][CH:21]=[C:22]([C:24]2[C:25]([CH2:35][O:36][CH3:37])=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:28]=2)[CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[NH2:38][C:19]1[N:20]=[CH:21][C:22]([C:24]2[C:25]([CH2:35][O:36][CH3:37])=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][N:32]([C:3](=[O:4])[CH2:2][OH:8])[CH2:31][CH2:30]3)[CH:28]=2)=[CH:23][C:18]=1[C:10]1[O:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 673881403-(1,3-Benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Product 1

HCID 42599839HCID 42599839, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

(2-chloro-2-oxo-ethyl)acetate (0.029 ml) was added in one portion to a stirred mixture of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (90 mg) and triethylamine (0.062 ml) in CH2Cl2 (5 ml) at 23° C. The resulting mixture was stirred at 23° C. for 2 hours and concentrated to dryness. Methanol (20 ml) and water (1 ml) were added to the residue followed by lithium hydroxide hydrateaqueous solution (0.334 g, 2M). The resulting solution was stirred at 23° C. After 4 hours the reaction mixture was concentrated and the crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanolic ammonia (7 N) in dichloromethane. The fractions were evaporated to dryness to afford 1-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-3-(methoxymethyl)pyrazol-1-yl]-1-piperidyl]-2-hydroxy-ethanone (42.0 mg) as a solid. NMR Spectrum: (DMSOd6): 1.77-1.87 (m, 1H), 1.88-2.00 (m, 1H), 2.05-2.14 (m, 2H), 2.79-2.89 (m, 1H), 3.11-3.21 (m, 1H), 3.41 (s, 3H), 3.78-3.88 (m, 1H), 4.08-4.21 (m, 2H), 4.40 (s, 2H), 4.41-4.51 (m, 2H), 4.58 (t, 1H), 7.40-7.48 (m, 2H), 7.66 (bs, 2H), 7.78 (dd, 1H), 7.84 (dd, 1H), 8.23 (s, 1H), 8.42 (d, 1H), 8.50 (d, 1H); Mass spectrum: M+H+ 463.

Workup

  1. concentrationconcentrated to dryness
  2. additionMethanol (20 ml) and water (1 ml) were added to the residue
  3. stirringThe resulting solution was stirred at 23° C
  4. concentrationAfter 4 hours the reaction mixture was concentrated
  5. customthe crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanolic ammonia (7 N) in dichloromethane
  6. customThe fractions were evaporated to dryness

Sources & evidence

ORD record
ord-1acf3505ed344bf19ff55beda75fef6c
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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