N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazol-2-amine → HCID 178480968, compound

HRID 897676Notes

Reaction equation

HRID 897676 reaction equation
IC1C2C(=NC=NC=2N)N([C@H]2CC[C@H](N3CCN(C)CC3)CC2)N=1.CC1(C)C(C)(C)OB(C2C=CC(NC3OC4C=CC=CC=4N=3)=CC=2)O1.[NH2:50][C:51]1[N:56]=[CH:55][N:54]=[C:53]2[N:57]([C@H:77]3[CH2:82][CH2:81][C@@H:80]([N:83]4[CH2:88][CH2:87][N:86]([CH3:89])[CH2:85][CH2:84]4)[CH2:79][CH2:78]3)[N:58]=[C:59]([C:60]3[CH:65]=[CH:64][C:63]([NH:66][C:67]4[O:68][C:69]5[CH:75]=[CH:74][CH:73]=[CH:72][C:70]=5[N:71]=4)=[C:62](F)[CH:61]=3)[C:52]=12>>[NH2:50][C:51]1[N:56]=[CH:55][N:54]=[C:53]2[N:57]([C@H:77]3[CH2:78][CH2:79][C@H:80]([N:83]4[CH2:84][CH2:85][N:86]([CH3:89])[CH2:87][CH2:88]4)[CH2:81][CH2:82]3)[N:58]=[C:59]([C:60]3[CH:61]=[CH:62][C:63]([NH:66][C:67]4[O:68][C:69]5[CH:75]=[CH:74][CH:73]=[CH:72][C:70]=5[N:71]=4)=[CH:64][CH:65]=3)[C:52]=12

Participants

4

Reactant 3

HCID 22346815N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazol-2-amineHCID 178480969HCID 178480969, compoundHCID 178481015HCID 178481015, compound

Product 1

HCID 178480968HCID 178480968, compound

Procedure

Trans-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-1,3-benzoxazol-2-amine was prepared from trans-3-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.036 g, 0.082 mmol) and N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazol-2-amine (0.034 g, 0.10 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}-2-fluorophenyl)-1,3-benzoxazol-2-amine. The compound was formed as an off-white powder (0.021 g, 50%): 1H NMR (DMSO-d6, 400 MHz) δ 10.86 (s, 1H), 8.23 (s, 1H), 7.93 (d, 2H), 7.66 (d, 2H), 7.51 (t, 1H), 7.25(t, 1H), 7.16 (t, 1H), 4.65 (m, 1H), 3.51 (m, 1H), 2.67-1.91 (m, 17H), 1.49-1.46 (m, 2H); 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=7.17 min., 100%; m/z 524 (MH+).

Sources & evidence

ORD record
ord-da5167bdda1340b5be1ad209ea4b70eb
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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