Trifluoroacetic acid → [6-(3-Amino-propoxy)-7-methoxy-quinazolin-4-yl]-[3-chloro-4-(pyridin-2-ylmethoxy)-phenyl]-amine

HRID 1725145Notes

Reaction equation

HRID 1725145 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[N:25]=[CH:24][N:23]=[C:22]2[NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)=[C:34]([Cl:46])[CH:33]=1)(C)(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[N:25]=[CH:24][N:23]=[C:22]2[NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)=[C:34]([Cl:46])[CH:33]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66623588(3-{4-[3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-methoxy-quinazolin-6-yloxy}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 66623957[6-(3-Amino-propoxy)-7-methoxy-quinazolin-4-yl]-[3-chloro-4-(pyridin-2-ylmethoxy)-phenyl]-amineYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

TFA (3 mL) was added drop wise to a suspension of (3-{4-[3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-methoxy-quinazolin-6-yloxy}-propyl)-carbamic acid tert-butyl ester (0.9 g, 1.59 mmol) in DCM (3 mL). Stir for 1 hour and the reaction mixture was diluted with DCM (20 ml) and sat. NaHCO3 (20 mL). Phases were separated and organic layer was extracted with DCM (20 mL). Organic layers were combined, dried (Na2SO4), and concentrated to give 0.7 g (95%) of desired product.

Workup

  1. customPhases were separated
  2. extractionorganic layer was extracted with DCM (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77dc6782c4c944ca82e09e31625deaf1
Source dataset
uspto-grants-2009_02
Patent number
US07488823B2

Reaction notes

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