Hydrochloric Acid → HCID 25121366, compound

HRID 1924420Notes

Reaction equation

HRID 1924420 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:13][N:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]1[N:25]1[CH2:29][CH2:28][S:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC=CC=1C.Cl>CN(C=O)C>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:13][N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]2[N:25]2[CH2:29][CH2:28][S:27][CH2:26]2)=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 1454243,5-Difluorophenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67521546HCID 67521546, compound

Product 1

HCID 25121366HCID 25121366, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Difluorophenylacetic acid (0.152 g, 0.88 mmol), 3-Amino-2-thiazolidin-3-yl-3H-quinazolin-4-one (0.146 g, 0.59 mmol) and HATU (0.268 g, 0.71 mmol) were dissolved in dry DMF (2.5 mL), followed by addition of 2,6-lutidine (205 μL, 1.76 mmol). The reaction mixture was stirred at RT for 48 h and then poured into 1 M HCl (20 mL). The formed precipitate was collected by filtration and washed with water and heptane, which after drying gave the title compound (0.180 g, 76%). LC-ESI-HRMS of [M+H]+ shows 403,1047 Da. Calc. 403,104028 Da.

Workup

  1. filtrationThe formed precipitate was collected by filtration
  2. washwashed with water and heptane, which
  3. customafter drying

Sources & evidence

ORD record
ord-eb03e69002b842f3bbeb3a2616dd34b0
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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