Sodium Carbonate → HCID 58699918, compound

HRID 2116782Notes

Reaction equation

HRID 2116782 reaction equation
Br[C:2]1[N:3]([CH2:24][C:25]#[C:26][CH3:27])[C:4]2[C:9](=[O:10])[N:8]([CH2:11][C:12]3[N:21]=[C:20]([CH3:22])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[N:7]=[CH:6][C:5]=2[N:23]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+].N1CCCC(NC(=O)OC(C)(C)C)C1>CS(C)=O.O>[CH2:24]([N:3]1[C:4]2[C:9](=[O:10])[N:8]([CH2:11][C:12]3[N:21]=[C:20]([CH3:22])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[N:7]=[CH:6][C:5]=2[N:23]=[C:2]1[N:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH2:29]1)[C:25]#[C:26][CH3:27]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 42330413-(Boc-amino)piperidineHCID 160377782-Bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

Product 1

HCID 58699918HCID 58699918, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 240 mg (0.57 mmol) 2-bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and 140 mg (0.70 mmol) tert-butyl (R)-piperidin-3-yl-carbamate in 4 ml dimethylsulphoxide was combined with 95 mg (0.90 mmol) sodium carbonate and stirred for 3 h at 80° C. Then another 50 mg tert-butyl piperidin-3-yl-carbamate was added and the mixture was stirred for a further 2 h at 80° C. After cooling to ambient temperature the mixture was combined with 10 ml of water and stirred for 30 minutes. The product thus precipitated was suction filtered, washed with 5 ml of water and dried.

Workup

  1. stirringthe mixture was stirred for a further 2 h at 80° C
  2. temperatureAfter cooling to ambient temperature the mixture
  3. stirringstirred for 30 minutes
  4. customThe product thus precipitated
  5. filtrationfiltered
  6. washwashed with 5 ml of water
  7. customdried

Sources & evidence

ORD record
ord-1ca4bf476dcb43afb19f13795d7188a2
Source dataset
uspto-grants-2008_10
Patent number
US07439370B2

Reaction notes

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