Oxalyl chloride → HCID 86692295, compound

HRID 1469838Notes

Reaction equation

HRID 1469838 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:16]3[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[Cl:24][C:25]1[C:30]([C:31](O)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:27][CH:26]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:24][C:25]1[C:30]([C:31]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[CH:9][N:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][C:2]([F:1])=[C:3]([C:20]([F:23])([F:21])[F:22])[CH:4]=2)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 71678384HCID 71678384, compound

Product 1

HCID 86692295HCID 86692295, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-(4-fluoro-3-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-45, 60 mg, 0.18 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 80 mg, 0.27 mmol), oxalyl chloride (52 mg, 0.41 mmol), DMF (1 drop) and DIPEA (70 mg, 0.54 mmol) in CH2Cl2 (2 mL) to afford 42 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.93 (s, 1H), 8.91 (d, J=7.8 Hz, 1H), 8.80 (s, 1H), 8.17 (d, J=7.2 Hz, 2H), 7.96 (t, 1H), 7.85 (m, 2H), 7.69 (t, J=9.6 Hz, 1H), 7.37 (m, 2H), 4.31 (d, J=5.4 Hz, 2H), 1.14 (s, 9H); MS (m/z): 593.10 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-253454f8f4604d7b9c21f08b14057579
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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