Oxalyl chloride → HCID 71677885, compound

HRID 1469827Notes

Reaction equation

HRID 1469827 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[C:22]2[C:17](=[C:18]([NH2:23])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.[Cl:24][C:25]1[C:30]([C:31](O)=[O:32])=[C:29]([F:34])[CH:28]=[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[CH:26]=[CH:27][CH:28]=[C:29]([F:34])[C:30]=1[C:31]([NH:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[N:16]=[CH:15][N:14]=[C:13]2[NH:12][C:3]1[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=1[F:1])=[O:32]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 679472-Chloro-6-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 86692282HCID 86692282, compound

Product 1

HCID 71677885HCID 71677885, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(2-fluoro-5-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-14, 60 mg, 0.18 mmol), 6-chloro-2-fluorobenzoic acid (48 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 45 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.69 (s, 1H), 10.16 (s, 1H), 8.80 (d, J=7.5 Hz, 1H), 8.57 (s, 1H), 8.23 (d, J=8.4 Hz, 1H), 8.02 (d, J=5.7 Hz, 1H), 7.74-7.68 (m, 2H), 7.63-7.51 (m, 2H), 7.44-7.36 (m, 2H); MS (m/z): 479.30 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-39f3322b6dd2425789a71dda7bb583fd
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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