Hydrochloric Acid → HCID 22484362, compound

HRID 1760544Notes

Reaction equation

HRID 1760544 reaction equation
C(OC(=O)[NH:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=2)=[C:24]([Cl:36])[CH:23]=1)(C)(C)C.Cl.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCCC1>[NH2:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=2)=[C:24]([Cl:36])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 69116127HCID 69116127, compound

Product 1

HCID 22484362HCID 22484362, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4.42 g of E-(3-{4-[3-chloro-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-carbamic acid tert-butyl ester in 21 mL of tetrahydrofuran was added 21 mL of 2 N hydrochloric acid. The mixture was heated at 60° C. for 3 hours, cooled to room temperature and basified with 10% aqueous potassium carbonate. Methylene chloride was added to the aqueous mixture and a solid precipitated. The solid was filtered and dried to yield 2.98 g of E-[6-(3-amino-propenyl)-quinazolin-4-yl]-[3-chloro-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine. 1H NMR (d6 DMSO): δ 8.62 (s, 1), 8.53 (m, 1), 8.26 (m, 2), 7.99 (m, 1), 7.89 (m, 1), 7.77 (m, 1), 7.30 (m, 3), 6.67 (m, 2), 3.44 (m, 2), 2.47 (s, 3).

Workup

  1. temperaturecooled to room temperature
  2. customa solid precipitated
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-4e691789ec144f80b88a8c7f8b14b561
Source dataset
uspto-grants-2005_01
Patent number
US06844349B2

Reaction notes

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