HCID 49839597, compound → HCID 57389342, compound

HRID 241172Notes

Reaction equation

HRID 241172 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:20][CH2:19][CH2:18][N:17]([C:21]5[C:30]6[C:25](=[CH:26][CH:27]=[C:28]([O:31]CC7C=CC=CC=7)[CH:29]=6)[N:24]=[CH:23][N:22]=5)[CH2:16][C:15]=4[CH:39]=3)[CH:9]=[CH:10][C:4]=2[N:3]=1>FC(F)(F)C(O)=O>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:20][CH2:19][CH2:18][N:17]([C:21]5[C:30]6[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=6)[N:24]=[CH:23][N:22]=5)[CH2:16][C:15]=4[CH:39]=3)[CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 49839597HCID 49839597, compound

Product 1

HCID 57389342HCID 57389342, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-(2-methyl-1H-benzimidazol-6-yl)-4-{6-[(phenylmethyl)oxy]quinazolin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepine (example 1) (26 mg, 0.05 mmol) in trifluoroacetic acid (3.0 mL) was heated to 68° C. for 3.5 hours then concentrated and dried. This material was then carried forward into step 2 without further purification. A sample of material obtained in this manner was purified by preparative reverse phase HPLC to give 4-[7-(2-methyl-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]quinazolin-6-ol. 1H NMR (400 MHz, d6-DMSO): 10.1 (s, 1H), 8.44 (s, 1H), 7.73 (d, 1H), 7.70 (d, 1H), 7.65 (d, 1H), 7.55-7.51 (m, 2H), 7.48 (d, 0.5H), 7.46 (d, 0.5H), 7.40 (dd, 1H), 7.33 (d, 1H), 7.04 (d, 1H), 5.00 (s, 2H), 4.46 (t, 2H), 4.24 (t, 2H), 2.54 (s, 3H). MS (EI) for C25H22N5O2: 424 (MH+).

Workup

  1. concentrationthen concentrated
  2. customdried
  3. customThis material was then carried forward into step 2 without further purification
  4. customA sample of material obtained in this manner
  5. customwas purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-5a76aae923fc4edcb224ba66fbe602a8
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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