Potassium Carbonate → HCID 68706946, compound

HRID 645523Notes

Reaction equation

HRID 645523 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:21](Cl)[N:20]=[C:19]([C:34]#[N:35])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:37]1[C:39]2([CH2:44][CH2:43][CH:42]([CH2:45][NH2:46])[CH2:41][CH2:40]2)[CH2:38]1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:21]([NH:46][CH2:45][CH:42]3[CH2:43][CH2:44][C:39]4([CH2:37][CH2:38]4)[CH2:40][CH2:41]3)[N:20]=[C:19]([C:34]#[N:35])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 68704587{spiro[2.5]octan-6-yl}methanamine hydrochlorideHCID 86627803HCID 86627803, compound

Product 1

HCID 68706946HCID 68706946, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[2-(5-benzylcarbamoyl-6-chloro-2-cyanopyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester (0.23 mmol) in CH3CN (5 mL), C-spiro[2.5]oct-6-yl-methylamine hydrochloride (0.25 mmol) and K2CO3 (0.7 mmol) are added at room temperature. After warmed up to 70° C., the reaction mixture is stirred over night. The mixture is diluted with H2O and AcOEt, and extracted twice with AcOEt. The organic layer is dried over Na2SO4, filtered, and concentrated to give 4-(2-{5-benzylcarbamoyl-2-cyano-6-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester as a white solid; 1H-NMR (CDCl3), δ 0.17-0.30 (4H, m), 0.89-1.06 (4H, m), 1.14-1.38 (3H, m), 1.46 (9H, s), 1.49-1.79 (9H, m), 2.51 (2H, br t), 3.42 (2H, t), 4.00 (2H, m), 4.45 (2H, t), 4.55 (2H, d), 7.30-7.39 (5H, m), 8.12 (1H, t), 10.16 (1H, t).

Workup

  1. extractionextracted twice with AcOEt
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-45dd79fcdb3e4fbcae9638e8227b413f
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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