Acetic Acid → 1-(1-Hydroxy-2-methylpropan-2-yl)-3-(4-(3-methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)phenylamino)quinazolin-6-yl)thiourea

HRID 240542Notes

Reaction equation

HRID 240542 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15]([NH:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[S:16])[CH:6]=[CH:7][C:8]=1[N:9]=[CH:10][N:11](C)C)#[N:2].[CH3:23][C:24]1[CH:25]=[C:26](N)[CH:27]=[CH:28][C:29]=1[O:30][C:31]1[CH:32]=[CH:33][C:34]2[O:38][C:37]([CH3:39])=[N:36][C:35]=2[CH:40]=1.C(O)(=O)C>C(OC(C)C)(=O)C>[OH:20][CH2:19][C:18]([NH:17][C:15]([NH:14][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[N:9]=[CH:10][N:11]=[C:1]2[NH:2][C:26]1[CH:27]=[CH:28][C:29]([O:30][C:31]2[CH:32]=[CH:33][C:34]3[O:38][C:37]([CH3:39])=[N:36][C:35]=3[CH:40]=2)=[C:24]([CH3:23])[CH:25]=1)=[S:16])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 669372733-Methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)benzenamineHCID 86650893(E)-N'-(2-cyano-4-(3-(1-hydroxy-2-methylpropan-2-yl)thioureido)phenyl)-N,N-dimethylformimidamide

Product 1

HCID 866508941-(1-Hydroxy-2-methylpropan-2-yl)-3-(4-(3-methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)phenylamino)quinazolin-6-yl)thioureaYield 62%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

To a solution of 1-(3-cyano-4-((dimethylamino)methyleneamino)phenyl)-3-(1-hydroxy-2-methylpropan-2-yl)thiourea (275 mg, 0.861 mmol) and 3-methyl-4-(2-methylbenzo[d]oxazol-5-yloxy)benzenamine (241 mg, 0.947 mmol) in isopropyl acetate (2 mL) was added acetic acid (0.2 mL, 3.44 mmol). After stirring at room temperature for 16 hours, hexanes was added and stirred with the mixture for 30 minutes. The mixture was filtered to provide the crude product (281 mg, 62%) as yellow solid.

Workup

  1. stirringstirred with the mixture for 30 minutes
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-8e88261bfc784b0fbafe56529078d75d
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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