Diisopropylethylamine → HCID 66763266, compound

HRID 578674Notes

Reaction equation

HRID 578674 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]([NH:37][C:38]2[C:47]3[C:42](=[C:43]([C:48]([NH2:50])=[O:49])[CH:44]=[CH:45][CH:46]=3)[N:41]=[CH:40][N:39]=2)[CH3:36])[CH:32]=[CH:33][CH:34]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:28][C:29]1[CH:30]=[C:31]([CH:35]([NH:37][C:38]2[C:47]3[C:42](=[C:43]([C:48]([NH2:50])=[O:49])[CH:44]=[CH:45][CH:46]=3)[N:41]=[CH:40][N:39]=2)[CH3:36])[CH:32]=[CH:33][CH:34]=1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27334013-Fluoro-4-methoxybenzoic acidHCID 66763381HCID 66763381, compound

Product 1

HCID 66763266HCID 66763266, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4-methoxybenzoic acid (26.00 mg; 0.15 mmol; 1.00 eq.) in DMF were added bis(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride (35.01 mg; 0.14 mmol; 0.90 eq.), 4-{[1-(3-aminophenyl)ethyl]amino}quinazoline-8-carboxamide (41.33 mg; 0.13 mmol; 0.88 eq.), and N-ethyl-N-isopropylpropan-2-amine (0.07 ml; 0.38 mmol; 2.50 eq.). The reaction mixture was stirred overnight at RT. Purified the crude by HPLC to obtain 20 mg of the title product in 28% yield. MS (M+1) 460

Workup

  1. customPurified the crude by HPLC

Sources & evidence

ORD record
ord-b6d0d3c1f2a948a9add41f03419f38c5
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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