4-Methylmorpholine → HCID 178522644, compound

HRID 1068877Notes

Reaction equation

HRID 1068877 reaction equation
CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:16]1[O:27][C:26]2[C:18](=[C:19]([CH:23]=[CH:24][CH:25]=2)[C:20]([OH:22])=O)[O:17]1.[NH2:28][C:29]1[C:37]2[C:32](=[N:33][CH:34]=[N:35][C:36]=2[NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=2)[NH:31][N:30]=1>C1COCC1.O>[Cl:45][C:41]1[CH:40]=[C:39]([NH:38][C:36]2[N:35]=[CH:34][N:33]=[C:32]3[NH:31][N:30]=[C:29]([NH:28][C:20](=[O:22])[C:19]4[CH:23]=[CH:24][CH:25]=[C:26]5[O:27][CH2:16][O:17][C:18]=45)[C:37]=23)[CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 178509242HCID 178509242, compound

Product 1

HCID 178522644HCID 178522644, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 320 μl (2.9 mmol) of NMM and 210 1 (1.6 mmol) of isobutyl chloroformate are added at −20° C. to 250 mg (1.5 mmol) of 2,3-methylenedioxybenzoic acid [for preparation see: Chem. Ber. 104 (1971) 2347] in 3.2 ml of THF and then stirred for 45 min. 378 mg (1.45 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine (see Step 1.6) are then added and the reaction mixture is allowed to rise to RT and is stirred for 1 hour to complete the reaction. The reaction mixture is poured into 100 ml of water and stirred for 1 hour, and the crude product is filtered off and washed with water and ethanol. Dissolution in 3 ml of DMSO at =110° C., cooling, filtering and washing with ethanol yield 4-(3chloro-phenylamino)-3-(2,3-methylenedioxy-benzoylamino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100/20)=16.5; FAB-MS: (M+H)+=409.

Workup

  1. customto rise to RT
  2. stirringis stirred for 1 hour
  3. customthe reaction
  4. stirringstirred for 1 hour
  5. filtrationthe crude product is filtered off
  6. washwashed with water and ethanol
  7. dissolutionDissolution in 3 ml of DMSO at =110° C.
  8. temperaturecooling
  9. filtrationfiltering
  10. washwashing with ethanol

Sources & evidence

ORD record
ord-e31252d2d8c445639500f69d5fb1e5c5
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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