4-Methylmorpholine → HCID 178453817, compound

HRID 1068885Notes

Reaction equation

HRID 1068885 reaction equation
C[N:2]1[CH2:7][CH2:6][O:5]CC1.Cl[C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10].[NH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[NH:19][N:18]=1.[C:34]1([CH3:40])[CH:39]=CC=C[CH:35]=1.C(OCC)(=O)C>C1COCC1.C(OCC)(=O)C>[Cl:33][C:29]1[CH:28]=[C:27]([NH:26][C:24]2[N:23]=[CH:22][N:21]=[C:20]3[NH:19][N:18]=[C:17]([NH:16][C:6](=[O:5])[CH:7]([NH:2][C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])[C:34]([CH3:40])([CH3:39])[CH3:35])[C:25]=23)[CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 21584019Toluene ethylacetateHCID 178509242HCID 178509242, compound

Product 1

HCID 178453817HCID 178453817, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Analogously to Example 5, 365 mg (1.58 mmol) of N-isobutyloxycarbonyl(D/L)-tert-leucine in 3.3 ml of THF and 347 μl (3.15 mmol) of NMM are activated with 226 μl (1.73 mmol) of isobutyl chloroformate and then reacted with 411 mg (1.58 mmol) of 3-amino-4-(3-chloro-phenylamino)1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) for 20 hours. Column chromatography (SiO2; toluene/ethyl acetate 1:1) and stirring in ethyl acetate/DIPE yield rac.-4-(3-chloro-phenylamino)-3-([2-isobutyloxycarbonylamino-3,3-dimethylbutyryl)-amino)-1 H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100/20)=15.5; FAB-MS: (M+H)+=474.

Sources & evidence

ORD record
ord-57d96c1457c541fd8ac7ce49dead77b9
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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