Isobutyric Acid → 1-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)-2-methylpropan-1-one

HRID 2091908Notes

Reaction equation

HRID 2091908 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:25][CH:26]([CH3:30])[C:27](O)=[O:28].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:27](=[O:28])[CH:26]([CH3:30])[CH3:25])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 6590Isobutyric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 584049524-(2-Chloro-6-(piperidin-4-ylmethyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 584049791-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Chloro-6-(piperidin-4-ylmethyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine from Example 148 (40 mg) was added to a pre-stirred (15 minutes) solution of 2-methylpropanoic acid (2 eq.), 1-Hydroxybenzotriazole (1.2), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.5 eq.), diisopropylethylamine (DIPEA, 5 eq.) in N,N-Dimethylformamide (0.9 mL). The reaction was stirred overnight then extracted with Ethyl Acetate and brine. The organic layer was dried (Mg2SO4), filtered and concentrated to give quantitative yield of 1-(4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)-2-methylpropan-1-one.

Workup

  1. extractionthen extracted with Ethyl Acetate and brine
  2. dry with materialThe organic layer was dried (Mg2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f746cf9c4da04a42be78e92f6e1799a5
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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