Diisopropylethylamine → 4-[1-(6-Methane sulfonyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 2066878Notes

Reaction equation

HRID 2066878 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.[NH:16]1[CH2:21][CH2:20][C:19](=[N:22][O:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[CH:33]([O:32][C:30]([N:27]1[CH2:28][CH2:29][CH:24]([O:23][N:22]=[C:19]2[CH2:18][CH2:17][N:16]([C:2]3[N:3]=[CH:4][C:5]4[CH2:11][N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:21][CH2:20]2)[CH2:25][CH2:26]1)=[O:31])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57461147Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylateHCID 866550182-Bromo-6-methanesulfonyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

Product 1

HCID 583334484-[1-(6-Methane sulfonyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 59a, 2d (51 mg) and diisopropylethylamine (0.07 mL) in 0.4 mL of DMSO was heated at 100° C. for 3 h. The mixture was cooled to room temperature, diluted with EtOAc (5 mL) and washed with brine (3×5 mL). The organic layer was dried, concentrated and purified by preparative HPLC to afford 59b: LC-MS 495.4 (MH+), tR=5.11 (Method 4). EC50: 328 nM.

Workup

  1. washwashed with brine (3×5 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-72d6a8c967b34e02a45b588040c9d169
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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