HCID 178462205, compound → HCID 178462166, compound

HRID 1068951Notes

Reaction equation

C([NH:8][C@H:9]([C:11]([NH:13][CH2:14][C:15]1[CH:16]=[C:17]([NH:21][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[N:28][C:29]=3[NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=3)[NH:24][N:23]=2)[CH:18]=[CH:19][CH:20]=1)=[O:12])[CH3:10])(OC(C)(C)C)=O>Cl>[Cl:38][C:34]1[CH:33]=[C:32]([NH:31][C:29]2[N:28]=[CH:27][N:26]=[C:25]3[NH:24][N:23]=[C:22]([NH:21][C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][NH:13][C:11](=[O:12])[C@H:9]([CH3:10])[NH2:8])[CH:16]=4)[C:30]=23)[CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 300 mg (0.554 mmol) of 3-[3-(N-{N-Boc-L-alanyl}-aminomethyl)-phenylamino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content 0.83 %; see Example 98) and 10 ml of 4N methanolic hydrochloric acid is stirred at 20° C. for 21 hours and then concentrated by evaporation in vacuo. Recrystallization of the residue from ethanol/diethyl ether yields 4-(3chloro-phenylamino)-3-[3-(N-{L-alanyl}-aminomethyl)-phenylamino]-1H-pyrazolo[3,4-d]pyrimidine.1.7 hydrochloride having a water content of 6.83%; m.p. 222-225° C.; ESI-MS: (M+H)+=437; [a]D20=+1.6±1.1° (c=0.893%, methanol).

Workup

concentrationconcentrated by evaporation in vacuo
customRecrystallization of the residue from ethanol/diethyl ether

Sources & evidence

ORD record: ord-608558c9dbb7409fbcdb3e12836b1c3c
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251911B1

Reaction notes

Loading…