2-Amino-4-methylphenol → HCID 178423562, compound

HRID 432392Notes

Reaction equation

HRID 432392 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[C:37]([OH:38])=[CH:36][CH:35]=[C:34]([CH3:39])[CH:33]=1.[NH2:40][C:41]1[N:46]=[CH:45][N:44]=[C:43]2[N:47]([C@H:67]3[CH2:72][CH2:71][C@@H:70]([N:73]4[CH2:78][CH2:77][N:76]([CH3:79])[CH2:75][CH2:74]4)[CH2:69][CH2:68]3)[N:48]=[C:49]([C:50]3[CH:55]=[CH:54][C:53]([NH:56][C:57]4OC5C=CC=C(C)C=5N=4)=[CH:52][CH:51]=3)[C:42]=12>>[NH2:40][C:41]1[N:46]=[CH:45][N:44]=[C:43]2[N:47]([C@H:67]3[CH2:72][CH2:71][C@@H:70]([N:73]4[CH2:74][CH2:75][N:76]([CH3:79])[CH2:77][CH2:78]4)[CH2:69][CH2:68]3)[N:48]=[C:49]([C:50]3[CH:55]=[CH:54][C:53]([NH:56][C:57]4[O:38][C:37]5[CH:36]=[CH:35][C:34]([CH3:39])=[CH:33][C:32]=5[N:31]=4)=[CH:52][CH:51]=3)[C:42]=12

Participants

4

Reactant 3

HCID 72642-Amino-4-methylphenolHCID 178424098HCID 178424098, compoundHCID 178480983HCID 178480983, compound

Product 1

HCID 178423562HCID 178423562, compound

Procedure

Cis-N2-(4-{4-Amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-methyl-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 (0.057 g, 0.140 mmol) and 2-amino-p-cresol (0.017 g, 0.140 mmol) in a manner similar to that used for 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. The compound was formed as an off-white solid (0.010 g, 13%): 1H NMR (DMSO-d6, 400 MHz) δ 10.81 (s, 1H), 8.23 (s, 1H), 7.93 (d, 2H), 7.66 (d, 2H), 7.38 (d, 1H), 7.30 (s, 1H), 6.96 (d, 1H), 4.80 (m, 1H), 2.60-2.07 (m, 12H), 2.39 (s, 3H), 2.15 (s, 3H), 1.71-1.59 (m, 5H); 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, 250×4.6 mm column) tr=7.48 min., 90%; m/z 538 (MH+).

Sources & evidence

ORD record
ord-9d013b327e2746ad97ea779f397f8bc1
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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