2-Amino-4,6-dichlorophenol → HCID 178480977, compound

HRID 432425Notes

Reaction equation

HRID 432425 reaction equation
NC1C=CC(C2C3C(=NC=NC=3N)N([C@H]3CC[C@@H](N4CCN(C)CC4)CC3)N=2)=CC=1.[NH2:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[C:33]=1[OH:40].[NH2:41][C:42]1[N:47]=[CH:46][N:45]=[C:44]2[N:48]([C@H:68]3[CH2:73][CH2:72][C@@H:71]([N:74]4[CH2:79][CH2:78][N:77]([CH3:80])[CH2:76][CH2:75]4)[CH2:70][CH2:69]3)[N:49]=[C:50]([C:51]3[CH:56]=[CH:55][C:54]([NH:57][C:58]4OC5C=CC=C(C)C=5N=4)=[CH:53][CH:52]=3)[C:43]=12>>[NH2:41][C:42]1[N:47]=[CH:46][N:45]=[C:44]2[N:48]([C@H:68]3[CH2:73][CH2:72][C@@H:71]([N:74]4[CH2:75][CH2:76][N:77]([CH3:80])[CH2:78][CH2:79]4)[CH2:70][CH2:69]3)[N:49]=[C:50]([C:51]3[CH:56]=[CH:55][C:54]([NH:57][C:58]4[O:40][C:33]5[C:34]([Cl:39])=[CH:35][C:36]([Cl:38])=[CH:37][C:32]=5[N:31]=4)=[CH:53][CH:52]=3)[C:43]=12

Participants

4

Reactant 3

HCID 106992-Amino-4,6-dichlorophenolHCID 178424098HCID 178424098, compoundHCID 178480983HCID 178480983, compound

Product 1

HCID 178480977HCID 178480977, compound

Procedure

cis-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dichloro-1,3-benzoxazol-2-amine was prepared from cis-3-(4-aminophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.100 g, 0.245 mmol) and 2-amino-4,6-dichlorophenol (0.044 g, 0.245 mmol) in a manner similar to that used in the synthesis of cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-4-methyl-1,3-benzoxazol-2-amine (PH4042235). The compound was formed as an off-white solid (0.008 g, 6%): RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 100 Å, 5 μm, 250×4.6 mm column) tr=8.93 min., 95%; m/z 594 (MH+).

Sources & evidence

ORD record
ord-0b098b9e4ae243a3a1d81e54fea645d8
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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