Oxalyl chloride → HCID 71679715, compound

HRID 1469844Notes

Reaction equation

HRID 1469844 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[C:5]([NH2:18])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:19][C:20]1[C:25]([C:26](O)=[O:27])=[C:24]([F:29])[C:23]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:22][CH:21]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:19][C:20]1[C:25]([C:26]([NH:18][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([CH3:1])[N:11]=[C:10]3[N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:27])=[C:24]([F:29])[C:23]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:35])([CH3:34])[CH3:36])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692298HCID 86692298, compound

Product 1

HCID 71679715HCID 71679715, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 2-methyl-4-morpholinoquinazolin-8-amine (Intermediate-51, 100 mg, 0.41 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 176 mg, 0.61 mmol), oxalyl chloride (115 mg, 0.92 mmol), DMF (1 drop) and DIPEA (159 mg, 1.23 mmol) in CH2Cl2 (5 mL) to afford 53 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.36 (s, 1H), 8.69 (d, J=7.6 Hz, 1H), 8.14-8.11 (t, J=5.7 Hz, 1H), 7.76-7.74 (d, J=8.4 Hz, 1H), 7.50-7.46 (t, J=8.1 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.37-7.33 (t, J=8.0 Hz, 1H), 4.30 (d, J=5.7 Hz, 2H), 3.77 (d, J=4.7 Hz, 2H), 3.73 (d, J=4.6 Hz, 2H), 3.30 (s, 3H), 1.13 (s, 9H); MS (m/z): 514.29 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-5a0c09d615dc4d18a6e78e5b21cf1f07
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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