Oxalyl chloride → HCID 71679712, compound

HRID 1469840Notes

Reaction equation

HRID 1469840 reaction equation
[CH3:1][C:2]1([CH3:21])[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[CH2:4][CH2:3][C:2]([CH3:21])([CH3:1])[CH2:7][CH2:6]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 86692296HCID 86692296, compound

Product 1

HCID 71679712HCID 71679712, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(4,4-dimethylcyclohexyl)-2-methylquinazoline-4,8-diamine (Intermediate-47, 180 mg, 0.63 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 271 mg, 0.95 mmol), oxalyl chloride (180 mg, 1.43 mmol), DMF (1 drop) and DIPEA (244 mg, 1.89 mmol) in CH2Cl2 (8 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.18 (s, 1H), 8.66 (d, J=7.8 Hz, 1H), 8.14 (t, 1H), 8.02 (d, J=8.1 Hz, 1H), 7.93 (d, 1H), 7.43 (m, 2H), 7.37 (d, J=7.8 Hz, 1H), 4.31 (d, 2H), 4.17 (m, 1H), 2.44 (s, 3H), 1.72 (m, 2H), 1.64-1.60 (m, 2H), 1.41-1.28 (m, 4H), 1.14 (s, 9H), 0.98 (s, 3H), 0.94 (s, 3H); MS (m/z): 554.35 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2bc99a558f3c4a79b6b278a1aa7b3727
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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