Hydrochloric Acid → Methyl 4-methyl-3-[({4-[(4-phenylquinazolin-2-yl)amino]phenyl}carbonyl)amino]benzenecarboximidoate

HRID 406835Notes

Reaction equation

HRID 406835 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:36])=[C:8]([NH:10][C:11](=[O:35])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:14][CH:13]=2)[CH:9]=1)#[N:3].[CH2:37]([OH:39])C>>[CH3:36][C:7]1[CH:6]=[CH:5][C:4]([C:2](=[NH:3])[O:39][CH3:37])=[CH:9][C:8]=1[NH:10][C:11]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:28]=[C:27]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:14][CH:13]=1)=[O:35]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 57662918N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

Product 1

HCID 57663019Methyl 4-methyl-3-[({4-[(4-phenylquinazolin-2-yl)amino]phenyl}carbonyl)amino]benzenecarboximidoateYield 100%

Procedure

Anhydrous hydrochloric acid gas was bubbled into a suspension of N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (273 mg, 0.60 mmol), prepared as described in Example 10, in absolute ethanol (5 mL) for 10 min and the flask was affixed with a drying tube and allowed to stand in the refrigerator overnight. The reaction was concentrated on a rotary evaporator to give methyl 4-methyl-3-[({4-[(4-phenylquinazolin-2-yl)amino]phenyl}carbonyl)amino]benzenecarboximidoate as a yellow solid (311 mg, 100%). 1H NMR (400 MHz, DMSO-d6): δ 11.90 (br s, 1H), 11.20 (br s, 1H), 10.40 (s, 1H), 9.95 (s, 1H), 8.20 (t, 2H), 8.03 (t, 2H), 7.87 (m, 3H), 7.82 (m, 3H), 7.65 (t, 3H), 7.43 (dt, 1H), 7.38 (d, 1H), 4.30 (s, 3H), 2.42 (s, 3H). MS (EI) for C30H25N5O2: 488.1 (MH+).

Workup

  1. customprepared
  2. customthe flask was affixed with a drying tube
  3. customto stand in the refrigerator overnight
  4. concentrationThe reaction was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-27163ed141a24b5c8c8d41b3c39d7c13
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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