Oxalyl chloride → HCID 71679879, compound

HRID 1469846Notes

Reaction equation

HRID 1469846 reaction equation
[F:1][C:2]1([F:21])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH2:19])[CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([CH3:20])[N:10]=2)[CH2:4][CH2:3]1.[Cl:22][C:23]1[C:28]([C:29](O)=[O:30])=[C:27]([F:32])[C:26]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:25][CH:24]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:22][C:23]1[C:28]([C:29]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[C:11]([CH3:20])[N:10]=[C:9]3[NH:8][CH:5]2[CH2:6][CH2:7][C:2]([F:1])([F:21])[CH2:3][CH2:4]2)=[O:30])=[C:27]([F:32])[C:26]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692300HCID 86692300, compound

Product 1

HCID 71679879HCID 71679879, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(4,4-difluorocyclohexyl)-2-methylquinazoline-4,8-diamine (Intermediate-53, 100 mg, 0.342 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 147 mg, 0.513 mmol), oxalyl chloride (97 mg, 0.77 mmol), DMF (1 drop) and DIPEA (132 mg, 1.026 mmol) in CH2Cl2 (3 mL) to afford 46 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.25 (s, 1H), 8.68 (d, J=7.6 Hz, 1H), 8.18-8.15 (t, J=5.8 Hz, 1H), 8.06-8.04 (d, J=8.4 Hz, 1H), 7.97-7.95 (d, J=7.6 Hz, 1H), 7.48-7.42 (m, 2H), 7.38-7.36 (d, J=8.0 Hz, 1H), 4.44 (m, 1H), 4.30 (d, J=5.6 Hz, 2H), 2.46 (s, 3H), 2.10-1.99 (m, 6H), 1.76-1.73 (m, 2H), 1.14 (s, 9H); MS (m/z): 562.32 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a08680103df7431997d8818f5e7f7ba0
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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