Morpholine → HCID 59199318, compound

HRID 2079679Notes

Reaction equation

HRID 2079679 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]2[N:21]=[CH:20][C:19]3[C:14](=[C:15]([O:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[CH:16]=[CH:17][C:18]=3[Cl:22])[N:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]2[N:21]=[CH:20][C:19]3[C:14](=[C:15]([O:23][CH:24]4[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]4)[CH:16]=[CH:17][C:18]=3[Cl:22])[N:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:6]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59199229HCID 59199229, compound

Product 1

HCID 59199318HCID 59199318, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-chloro-4-(5-chloro-8-(piperidin-4-yloxy) quinazolin-2-ylamino) benzoic acid (1 eq), morpholine (3 eq), HATU (1.5 eq) and DIEA (4 eq) in NMP was stirred at room temperature for 4 h. The reaction mixture was concentrated and purified by semi-prep HPLC to provide pure product in 50% yield. ES/MS m/z 502.3 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by semi-prep HPLC
  3. customto provide pure product in 50% yield

Sources & evidence

ORD record
ord-5ee9669b757b46c1bdc3fec78987ae39
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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