Hydrochloric Acid → [6-(2-Aminomethyl-thiazol-4-yl)-quinazolin-4-yl]-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine

HRID 415012Notes

Reaction equation

HRID 415012 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][N:18]=[C:17]3[NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[C:27]([CH3:39])[CH:26]=2)[N:13]=1)(C)(C)C.Cl.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.O>[NH2:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][N:18]=[C:17]3[NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[C:27]([CH3:39])[CH:26]=2)[N:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 131727277(4-{4-[3-Methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]quinazolin-6-yl}-thiazol-2-ylmethyl)-carbamic acid ter-butyl ester

Product 1

HCID 66623689[6-(2-Aminomethyl-thiazol-4-yl)-quinazolin-4-yl]-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amineYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-{4-[3-Methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]quinazolin-6-yl}-thiazol-2-ylmethyl)-carbamic acid ter-butyl ester (81 mg, 0.14 mmol) is treated with concentrated aqueous hydrochloric acid (0.5 ml) in EtOAc (6 ml). Reaction progress is followed by LC/MS. Upon reaction completion saturated aqueous potassium carbonate solution is added, the reaction mixture is diluted with water and thoroughly extracted with DCM and EtOAc. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure to yield 45 mg (0.095 mmol, 68%) of clean desired product.

Workup

  1. customReaction progress
  2. additionis added
  3. extractionthoroughly extracted with DCM and EtOAc
  4. dry with materialThe combined organic extracts are dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c8603f6fa444230998d02e999704ba4
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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