Triethylamine → HCID 136121383, compound

HRID 2079327Notes

Reaction equation

HRID 2079327 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[OH:23])[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH:24][CH:25]([CH2:29][CH2:30]CC)[C:26]([OH:28])=O.[CH2:33](N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:24][C:25]([CH3:33])([CH2:29][CH3:30])[C:26]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[OH:23])[N:8]=2)[CH2:6][CH2:5]1)=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 998242-Hydroxyhexanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1361053622-(4-(Piperazin-1-yl)quinazolin-2-yl)phenol

Product 1

HCID 136121383HCID 136121383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(4-(piperazin-1-yl)quinazolin-2-yl)phenol (70 mg, 0.23 mmol) in DMF (0.5 mL) was added to 2-hydroxyhexanoic acid (39.3 mg, 0.297 mmol). Triethylamine (63 μL) was added at room temperature, then a solution of HATU (113 mg) in 0.5 mL DMF. The reaction was stirred overnight. Purification using reverse phase HPLC (10-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) gave 2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-methylbutan-1-one. LC/MS: m/z 421.3 (M+H)+ at 2.60 min (10%-99% CH3CN (0:035% TFA)/H2O (0.05% TFA)).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-e9e942f8a1c543739f84664245119587
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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