HCID 20817109, compound → HCID 178437379, compound
Reaction equation
B([O-])[O-].IC1C2C(=NC=NC=2N)N([C@H]2CC[C@@H](N3CCN(C)CC3)CC2)N=1.[NH2:28][C:29]1[N:34]=[CH:33][N:32]=[C:31]2[N:35]([CH:55]3[CH2:60][CH2:59][CH:58]([N:61]4[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]4)[CH2:57][CH2:56]3)[N:36]=[C:37]([C:38]3[CH:43]=[CH:42][C:41]([NH:44][C:45]4[S:46][C:47]5C=C(Cl)[CH:51]=[CH:50][C:48]=5[N:49]=4)=[CH:40][CH:39]=3)[C:30]=12>>[NH2:28][C:29]1[N:34]=[CH:33][N:32]=[C:31]2[N:35]([C@H:55]3[CH2:60][CH2:59][C@@H:58]([N:61]4[CH2:66][CH2:65][N:64]([CH3:67])[CH2:63][CH2:62]4)[CH2:57][CH2:56]3)[N:36]=[C:37]([C:38]3[CH:39]=[CH:40][C:41]([NH:44][C:45]4[S:46][CH:47]=[C:48]([CH2:50][CH3:51])[N:49]=4)=[CH:42][CH:43]=3)[C:30]=12Participants
Procedure
The boronate intermediate (0.15 g, 0.45 mmol) was coupled with cis-3-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.182 g, 0.41 mmol) using the procedure for Suzuki coupling described in the preparation of N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-6-chloro-1,3-benzothiazol-2-amine. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 7.0-8.0 min) afforded cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-4-ethyl-1,3-thiazol-2-amine as an off-white powder (0.069 g, 0.133 mmol); RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 7.05 min; MS (MH)+ 518.
Workup
- customPurification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min
Sources & evidence
- ORD record
- ord-591502b230cf4c799650896860f894da
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921763B2
Reaction notes
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