Tetrahydrofuran → 1-[3-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-yl]-3-{3-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy]phenyl}urea

HRID 631530Notes

Reaction equation

HRID 631530 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][C:13](=[O:15])[O-])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][O:31][CH3:32])[N:24]=[CH:23][N:22]=[C:21]2[O:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37].C(N(CC)[CH:45]([CH3:47])[CH3:46])(C)C.C1C[O:53][CH2:52][CH2:51]1>>[CH2:52]([O:53][C:45]([C:9]1[CH:10]=[C:11]([NH:12][C:13]([NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[C:34]([O:33][C:21]3[C:20]4[C:25](=[CH:26][C:27]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[C:18]([O:17][CH3:16])[CH:19]=4)[N:24]=[CH:23][N:22]=3)[CH:35]=2)=[O:15])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)([CH3:46])[CH3:47])[CH3:51]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 668758053-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)anilineHCID 131735419HCID 131735419, compound

Product 1

HCID 582678641-[3-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-yl]-3-{3-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy]phenyl}ureaYield 57%

Procedure

Using the procedure described in Example 159B, phenyl 342-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-ylcarbamate described in Example 168B (0.115 g, 0.33 mmol), 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline from Example 117B (0.112 g, 0.33 mmol), and N,N-diisopropylethylamine (0.8 mL) in THF (6 mL) at 50° C. for 5 hours, to afford 1-[3-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-yl]-3-{3-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy]phenyl}urea as solid (0.116 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 9.25 (br, 1H), 8.55 (s, 2H), 7.56 (m, 6H), 7.41 (m, 3H), 7.18 (d, 1H), 6.94 (d, 1H), 6.41 (s, 1H), 4.34 (m, 2H), 3.98 (s, 3H), 3.77 (m, 2H), 3.35 (s, 3H), 3.24 (q, 2H), 1.46 (s, 6H), 1.03 (t, 3H); LC-MS (ESI) m/z 567 (M-OEt)+.

Sources & evidence

ORD record
ord-a09d6bc3d8194f39aab1bd60690a3b8f
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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