Ether hydrochloride → 1-{3-[6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio]phenyl}-3-(5-tert-butylisoxazol-3-yl)urea hydrochloride

HRID 631301Notes

Reaction equation

HRID 631301 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[S:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:31][C:32]2[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:34][N:33]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1.[ClH:41].CCOCC>C(Cl)Cl.CO>[ClH:41].[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[S:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:31][C:32]2[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:34][N:33]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 582679381-{3-[6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio]phenyl}-3-(5-tert-butylisoxazol-3-yl)urea

Product 1

HCID 668768501-{3-[6,7-Bis(2-methoxyethoxy)quinazolin-4-ylthio]phenyl}-3-(5-tert-butylisoxazol-3-yl)urea hydrochlorideYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

As described in Example 6B Step 2, to a solution of 1-{3-[6,7-bis(2-methoxyethoxy)quinazolin-4-ylthio]phenyl}-3-(5-tert-butylisoxazol-3-yl)urea in CH2Cl2 and MeOH was added 1.0 M HCl/Et2O solution (2 eq.), to afford 1-{3-[6,7-bis(2-methoxyethoxy)quinazolin-4-ylthio]phenyl}-3-(5-tert-butylisoxazol-3-yl)urea hydrochloride as solid (0.098 g, 40%). 1H NMR (300 MHz, DMSO-d6) δ 9.66 (s, 1H), 9.23 (s, 1H), 8.72 (s, 1H), 7.85 (s, 1H), 7.52 (d, 1H), 7.44 (t, 1H), 7.44 (s, 1H), 7.38 (s, 1H), 7.28 (d, 1H), 6.49 (s, 1H), 4.35 (m, 4H), 3.78 (m, 4H), 3.37 (s, 3H), 3.35 (s, 3H), 1.28 (s, 9H); LC-MS (ESI) m/z 568 (M+H)+.

Sources & evidence

ORD record
ord-eeba398734bf4e92bf110ca880bf95a3
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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