Morpholine → HCID 58346405, compound

HRID 222024Notes

Reaction equation

CS(O[CH2:6][CH2:7][N:8]1[C:16]2[CH2:15][CH2:14][C:13]3[C:17]4[C:23]([NH:24][C:25]5[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]6[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=6)=[C:27]([Cl:40])[CH:26]=5)=[N:22][CH:21]=[N:20][C:18]=4[S:19][C:12]=3[C:11]=2[CH:10]=[N:9]1)(=O)=O.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C(N(C(C)C)CC)(C)C>CC#N>[Cl:40][C:27]1[CH:26]=[C:25]([NH:24][C:23]2[N:22]=[CH:21][N:20]=[C:18]3[S:19][C:12]4[C:11]5[CH:10]=[N:9][N:8]([CH2:7][CH2:6][N:41]6[CH2:46][CH2:45][O:44][CH2:43][CH2:42]6)[C:16]=5[CH2:15][CH2:14][C:13]=4[C:17]=23)[CH:30]=[CH:29][C:28]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 2 mL CH3CN were sequentially added 2-[6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-4,5-dihydro-3H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-3-yl]ethyl methanesulfonate (80 mg, 0.13 mmol), morpholine (18 mg, 0.20 mmol), and diisopropylethylamine (35 mg, 0.27 mmol). The reaction mixture was then heated up to 70° C. for 14 h. Upon cooling down, the crude was purified by HPLC to afford the desired product as an off-white solid (45 mg, 54%). 1H-NMR (DMSO-d6) δ 8.38 (s, 1H), 7.80 (d, 1H), 7.53 (s, 1H), 7.44 (dd, 1H), 7.38 (m, 1H), 7.24 (m, 2H), 7.04 (td, 1H), 6.98 (d, 1H), 6.95 (s, 1H), 5.13 (s, 2H), 4.18 (t, 2H), 3.63 (t, 4H), 3.35 (t, 2H), 3.14 (t, 2H), 2.78 (t, 2H), 2.45 (t, 4H); LCMS RT=2.72 min; [M+H]+=591.2.

Workup

temperatureUpon cooling down
customthe crude was purified by HPLC

Sources & evidence

ORD record: ord-e8cc63fec8a74eeb9e4178d5db919e72
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207172B2

Reaction notes

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