Diisopropylethylamine → HCID 136237294, compound

HRID 713519Notes

Reaction equation

HRID 713519 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]1)=[O:8].[CH:19]1([CH2:22][NH:23][CH2:24][C:25]2[NH:26][C:27](=[O:35])[C:28]3[CH2:34][O:33][CH2:32][CH2:31][C:29]=3[N:30]=2)[CH2:21][CH2:20]1.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>CN(C=O)C.C(Cl)Cl>[CH:19]1([CH2:22][N:23]([CH2:24][C:25]2[NH:26][C:27](=[O:35])[C:28]3[CH2:34][O:33][CH2:32][CH2:31][C:29]=3[N:30]=2)[C:16](=[O:18])[CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:8])[CH2:14][CH2:13]2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71226873HCID 71226873, compoundHCID 1362440742-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one

Product 1

HCID 136237294HCID 136237294, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound [4-(pyridine-2-carbonyl)-piperidin-1-yl]-acetic acid (178 mg, 0.72 mmol) and 2-[(cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (169 mg, 0.72 mmol) in DMF (5 mL) and DCM (5 mL) at 0° C. is added DIPEA (0.50 mL, 2.87 mmol) and then HATU (313 mg, 0.82 mmol). The reaction is then stirred at 25° C. for 36 hours. The solvent was removed under vacuum and then solubilized in methanol and filtered. The compound was then purified by reverse phase using sunfire C18 ODB using water acetonitrile and TFA as a buffer to afford the title compound (140 mg). 1H NMR (400 MHz, MeOD) δ: 8.68 (s, 1H), 7.99 (m, 2H), 7.59 (s, 1H), 4.68 (s, 1H), 4.57 (s, 2H), 4.49 (s, 1H), 3.97 (t, J=5.6 Hz, 3H), 3.51 (d, J=7.1 Hz, 1H), 3.40 (s, 2H), 3.36 (s, 2H), 3.35-3.31 (m, 2H), 3.30 (d, J=11.6 Hz, 2H), 2.68-2.58 (m, 2H), 2.37-2.24 (m, 2H), 1.96-1.91 (m, 2H), 1.13-0.97 (m, 1H), 0.62-0.45 (m, 2H), 0.33-0.22 (m, 2H). HRMS calculated for C25H31N5O4=465, 2376. found (ESI, [M+H]+), 465, 2369. LRMS m/z: ES+=466.0 (M+H), retention time 1.04.

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationfiltered
  3. customThe compound was then purified by reverse phase

Sources & evidence

ORD record
ord-c7ccbe5aa7ff4620a5aa3d171d248d05
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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