Oxalyl chloride → HCID 71679057, compound

HRID 1469821Notes

Reaction equation

HRID 1469821 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1.[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:15][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[CH:7][N:6]=[C:5]3[O:4][C:3]2[CH:16]=[C:17]([C:20]([F:22])([F:23])[F:21])[CH:18]=[CH:19][C:2]=2[F:1])=[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 71678212HCID 71678212, compound

Product 1

HCID 71679057HCID 71679057, compoundYield 13.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-(2-fluoro-5-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-22, 300 mg, 0.93 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 322 mg, 1.12 mmol), oxalyl chloride (212 mg, 1.68 mmol), DMF (1 drop) and DIPEA (360 mg, 2.79 mmol) in CH2Cl2 (10 mL) to afford 75 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.97 (s, 1H), 8.92-8.90 (d, J=7.2 Hz, 1H), 8.81 (s, 1H), 8.19-8.10 (m, 3H), 7.89-7.84 (m, 2H), 7.77-7.71 (t, J=9.9 Hz, 1H), 7.40-7.32 (m, 2H), 4.31-4.29 (d, J=6.0 Hz, 2H), 1.13 (s, 9H); MS (m/z): 593.31 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-75d58648d9aa4ac2bc9f886d06aa95ff
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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