Ethanol → HCID 178462187, compound

HRID 1068879Notes

Reaction equation

HRID 1068879 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.[CH2:34](O)C.[CH2:37]1[CH2:41]OC[CH2:38]1>CS(C)=O>[CH2:12]([O:11][C:9]([NH:2][C@H:7]([C:6]([NH: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)=[O:5])[CH3:34])=[O:10])[C:13]1[CH:15]=[CH:41][CH:37]=[CH:38][CH:14]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 178509242HCID 178509242, compound

Product 1

HCID 178462187HCID 178462187, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Analogously to Example 5, 514 mg (2.3 mmol) of N-benzyloxycarbonyl-(D/L)-alanine in 4.8 ml of THF and 506 μl (4.6 mmol) of NMM are activated with 349 1 (2.6 mmol) of isobutyl chloroformate and then reacted with 600 mg (2.3 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). Dissolution of the crude product in 2 ml of DMSO at 100° C., addition of 30 ml of ethanol and cooling yield rac.-3-{(N-benzyloxycarbonyl-alanyl)-amino}-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; mp. 238-240° C.; HPLC: tRet(grad20-100/20)=13.5; FAB-MS: (M+H)+=466.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-a6858cbfa1fb460d8ece435843533255
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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