Dimethylformamide → HCID 86710185, compound

HRID 2284419Notes

Reaction equation

HRID 2284419 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[N:13][C:14]([C:18]4[CH:19]=[N:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:22][CH:23]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH:38][C:39]([CH3:44])([CH3:43])[C:40](O)=[O:41].CN(C=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O>[OH:38][C:39]([CH3:44])([CH3:43])[C:40]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)=[N:13][C:14]([C:18]4[CH:19]=[N:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[N:22][CH:23]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)=[O:41]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 116712-Hydroxyisobutyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86710183HCID 86710183, compound

Product 1

HCID 86710185HCID 86710185, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 25 mL round bottom flask, tert-butyl (5-(7-(3-aminophenyl)-4-morpholinoquinazolin-2-yl)pyrimidin-2-yl)carbamate (0.1 g, 0.0002 mol), 2-hydroxy-2-methylpropanoic acid (0.052 g, 0.0005 mol) and DMF (10 mL) were added. To the flask, HATU (0.152 g, 0.0004 mol) and TEA (0.081 mL, 0.0006 mol) were added and then stirred at room temperature for 12 hours. To the reaction mixture was added water to provide a precipitate. The precipitate was collected by filtration to provide the crude product. The crude product was purified by flash column chromatography (2% methanol in chloroform) to obtain the title compound (0.06 g, 60%). LC-MS (ESI) Calculated mass. 585.2, Observed mass [M+H]+: 586.1 (RT=0.83 min).

Workup

  1. customto provide a precipitate
  2. filtrationThe precipitate was collected by filtration
  3. customto provide the crude product
  4. customThe crude product was purified by flash column chromatography (2% methanol in chloroform)

Sources & evidence

ORD record
ord-4a24541a44f44568bf7080785da3fab4
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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