Trifluoroacetic acid → [6-(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-[3-methyl-4-(pyridin-3-yloxy)-phenyl]-amine

HRID 584565Notes

Reaction equation

HRID 584565 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH:13]2[CH:9]1[CH2:10][N:11]([C:14]1[N:38]=[CH:37][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[C:25]([CH3:36])[CH:24]=4)[C:16]=3[CH:15]=1)[CH2:12]2)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][CH:8]1[CH:9]2[CH:13]1[CH2:12][N:11]([C:14]1[N:38]=[CH:37][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[C:25]([CH3:36])[CH:24]=4)[C:16]=3[CH:15]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11249486(3-{4-[3-Methyl-4-(pyridin-3-yloxy)-phenylamino]-pyrido[3,4-d]pyrimidin-6-yl}-3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester

Product 1

HCID 10224262[6-(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrido[3,4-d]pyrimidin-4-yl]-[3-methyl-4-(pyridin-3-yloxy)-phenyl]-amineYield 98.8%

Procedure

A sample (0.26 g, 0.49 mmol) of (3-{4-[3-Methyl-4-(pyridin-3-yloxy)-phenylamino]-pyrido[3,4-d]pyrimidin-6-yl}-3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester was treated with 0.5 mL of trifluoroacetic acid and immediately concentrated in vacuo. The residue was dissolved in chloroform and washed with saturated sodium bicarbonate. The aqueous layer was back extracted several times with chloroform. The organics were dried over sodium sulfate and evaporated to afford 206 mg of the title compound. A pure sample was obtained by crystallization from methanol and isopropyl ether. 1H NMR (CDCl3): δ 8.96 (s, 1), 8.53 (s, 1), 8.33 (m, 2), 7.65 (m, 1), 7.55 (m, 1), 7.21 (m, 2), 6.96 (d, 1), 615 (s, 1), 3.76 (d, 2), 3.54 (m, 2), 2.26 (s, 3), 2.24 (m, 1), 1.76 (m, 2). M.S. (m+1): 426. HPLC retention time (minutes): 3.919.

Workup

  1. concentrationimmediately concentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe organics were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2c0d8051515d4cd5bdc5ce467c99daf8
Source dataset
uspto-grants-2005_08
Patent number
US06927220B2

Reaction notes

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