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Water → 4-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

HRID 578628
Notes
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Reaction equation

HRID 578628 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1.C1N=C[N:28](C(N2C=NC=C2)=O)C=1.[NH4+].[Cl-].O>CS(C)=O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([NH2:28])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 667637834-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acid

Product 1

HCID 667623904-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-{[3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acid (68 mg, 0.19 mmol) in 2 mL of anhydrous DMSO, CDI (47 mg, 0.29 mmol, 1.5 equiv.) was added. The resulting mixture was stirred at 50° C. for 3 h. After cooling down to rt, NH4Cl (22 mg, 0.29 mmol, 1.5 equiv.) was added. The reaction mixture was stirred at rt overnight. The reaction mixture was poured into water. The white precipitate was collected as the desired product by filtration, followed by washed with water in 92% yield. 1HNMR (In DMSO): 4.90 (d, J=5.9 Hz, 2H), 7.56-7.69 (m, 4H), 7.74 (s, 1H), 7.86 (d, J=3.7 Hz, 1H), 8.51 (dd, J=1.5 and 8.0 Hz, 1H), 8.58 (dd, J=1.5 and 7.7 Hz, 1H), 8.59 (s, 1H), 9.24 (t, J=5.9 Hz, 1H), 10.33 (d, J=3.7 Hz, 1H). Mass: M+H+: 347.

Workup

  1. temperatureAfter cooling down to rt
  2. stirringThe reaction mixture was stirred at rt overnight
  3. filtrationThe white precipitate was collected as the desired product by filtration
  4. washby washed with water in 92% yield

Sources & evidence

ORD record
ord-08fdda18b1eb4494a41705b94017a1a6
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040560B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes