HCID 68465292, compound → HCID 86031658, compound

HRID 503705Notes

Reaction equation

HRID 503705 reaction equation
C(OC(=O)NCC(O)[CH:10]([OH:36])[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:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:24]([CH3:35])[CH:23]=1)(C)(C)C>C(Cl)Cl>[CH3:35][C:24]1[CH:23]=[C:22]([NH:21][C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([CH:10]=[O:36])[CH:12]=3)[N:17]=[CH:16][N:15]=2)[CH:27]=[CH:26][C:25]=1[O:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 1

HCID 68465292HCID 68465292, compound

Product 1

HCID 86031658HCID 86031658, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(3-Methyl-4-phenoxy-phenylamino)-quinazoline-6-carbaldehyde is prepared by adding NaIO4 (1.5 mL, 0.65 M in H2O) to a slurry of silica gel (1 g) in DCM (6 mL) followed by the addition of {2,3-dihydroxy-3-[4-(3-methyl-4-phenoxy-phenylamino)-quinazolin-6-yl]-propyl}-carbamic acid tert-butyl ester (from Step A, ˜0.64 mmol) in DCM (2 mL). The reaction mixture stirs for 1 hour, is filtered and washed with DCM (20 mL), and concentrated to give 280 mg of crude product. The product is used without further purification in Step E.

Workup

  1. filtrationis filtered
  2. washwashed with DCM (20 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-470bef4514f6468ab459f4cdc48fc487
Source dataset
uspto-grants-2010_08
Patent number
US07777032B2

Reaction notes

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