Trifluoroacetic acid → HCID 69910139, compound

HRID 352663Notes

Reaction equation

HRID 352663 reaction equation
C([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]#[C:26][CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:21]=3)[N:16]=[CH:15]2)=[CH:9][CH:8]=1)(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[N:28]1([CH2:27][C:26]#[C:25][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][N:14]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:34])=[O:5])=[CH:8][CH:9]=2)[C:23]3=[O:24])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20732840HCID 20732840, compound

Product 1

HCID 69910139HCID 69910139, compound

Procedure

4-[6-(3-Morpholin-4-yl-prop-1-ynyl)-4-oxo-4H-quinazolin-3-ylmethyl]-benzoic acid tert-butyl ester from the previous step was dissolved in 20 mL of trifluoroacetic acid (“TFA”), and stirred at room temperature for 30 minutes. The TFA was then evaporated in vacuum, and dissolved in dichloromethane. Hexane was then added, which precipitated 4-[6-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4H-quinazolin-3-ylmethyl]-benzoic acid trifluoroacetic acid salt as a solid (150 mg). Mass Spec: 404 (M+1), 460 (M+1+TFA). 1H-NMR. DMSO: 3.2-4.4 (broad m, 6H), 5.27 (s, 2H), 7.4 (d, J=8.3 Hz, 2H), 7.72 (d, J=8.6 Hz, 1H), 7.88 (s, 1H), 7.88-7.94 (m, 3H), 8.23 (d, J=1.4 Hz, 1H), 8.64 (s, 1H).

Workup

  1. customThe TFA was then evaporated in vacuum
  2. dissolutiondissolved in dichloromethane
  3. additionHexane was then added
  4. customwhich precipitated 4-[6-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4H-quinazolin-3-ylmethyl]-benzoic acid trifluoroacetic acid salt as a solid (150 mg)

Sources & evidence

ORD record
ord-d21b79ac55624af4b79d275c8f882533
Source dataset
uspto-grants-2004_06
Patent number
US06747147B2

Reaction notes

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