4-Methylmorpholine → HCID 178502211, compound

HRID 1068884Notes

Reaction equation

HRID 1068884 reaction equation
C[N:2]1CC[O:5][CH2:4][CH2:3]1.ClC(O[CH2:12][CH:13]([CH3:15])[CH3:14])=O.[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.C1(C)C=CC=CC=1.[C:41]([O:44][CH2:45]C)(=[O:43])C>C1COCC1>[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:4](=[O:5])[CH:3]([NH:2][C:41]([O:44][CH3:45])=[O:43])[C:13]([CH3:12])([CH3:14])[CH3:15])[C:25]=23)[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

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

Product 1

HCID 178502211HCID 178502211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 5, 283 mg (1.49 mmol) of N-methoxycarbonyl-(D/L)-tert-leucine in 3.3 ml of THF and 329 ;d (2.99 mmol) of NMM are activated with 214 μl (1.64 mmol) of isobutyl chloroformate and then reacted with 388 mg (1.49 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) yields rac.-4-(3-chloro-phenylamino)-3-([2-methoxycarbonylamino-3,3-dimethyl-butyryl]-amino)-1H-pyrazolo[3,4-d]-pyrimidine; HPLC: tRet(grad20-100/20)=12.1; FARMS: (M+H)+432.

Sources & evidence

ORD record
ord-c05d2fe10700493b96630dd723220e0a
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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