4-Methylmorpholine → HCID 178453816, compound

HRID 1068882Notes

Reaction equation

HRID 1068882 reaction equation
[CH2:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])[CH:2]([CH3:4])[CH3:3].CN1CCOCC1.ClC(OCC(C)C)=O.[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.C(O)C>[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:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[O:7])[C:37]=23)[CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 15162334HCID 15162334, compoundHCID 178509242HCID 178509242, compound

Product 1

HCID 178453816HCID 178453816, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 5. 502 mg (2.86 mmol) of N-isobutyloxycarbonyl-glycine in 5.9 ml of THF and 580 μl (5.3 mmol) of NMM are activated with 375 μl (2.86 mmol) of isobutyl chloroformate and then reacted with 745 mg (2.86 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). Stirring in 7.5 ml of boiling ethanol and filtering while hot yield 4-(3-chloro-phenylamino)-3-([N-iso-butyloxycarbonyl-glycyl]-amino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=12.8; FAB-MS: (M+H)+=418.

Workup

  1. filtrationfiltering

Sources & evidence

ORD record
ord-66f88790b5d44bc89f205fa37d98fdc2
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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