Oxalyl chloride → HCID 71680053, compound

HRID 1469851Notes

Reaction equation

HRID 1469851 reaction equation
[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH2:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[C:24]([C:25](O)=[O:26])=[C:23]([F:28])[C:22]([CH2:29][NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:21][CH:20]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:25](=[O:26])[C:24]3[C:19]([Cl:18])=[CH:20][CH:21]=[C:22]([CH2:29][NH:30][C:31](=[O:36])[C:32]([CH3:33])([CH3:34])[CH3:35])[C:23]=3[F:28])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692304HCID 86692304, compound

Product 1

HCID 71680053HCID 71680053, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(tert-butyl)-2-methylquinazoline-4,8-diamine (Intermediate-58, 100 mg, 0.43 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 150 mg, 0.52 mmol), oxalyl chloride (82 mg, 0.65 mmol), DMF (1 drop) and DIPEA (166 mg, 1.29 mmol) in CH2Cl2 (3 mL) to afford 46 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.21 (s, 1H), 8.66 (d, J=7.4 Hz, 1H), 8.15 (t, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.44-7.33 (m, 4H), 4.31 (d, J=5.8 Hz, 2H), 2.48 (s, 3H), 1.14 (s, 9H); MS (m/z): 500.60 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-5a887e0067f94653a1d09dc1a1af6631
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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