Thionyl Chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-5-(pivalamidomethyl)benzamide

HRID 1469853Notes

Reaction equation

HRID 1469853 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]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:23][C:19]=1[C:20](O)=[O:21].S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C1COCC1>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:20](=[O:21])[C:19]3[CH:23]=[C:24]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH:25]=[CH:26][C:18]=3[Cl:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

Product 1

HCID 71680054N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-5-(pivalamidomethyl)benzamideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(tert-butyl)quinazoline-4,8-diamine (Intermediate-55, 50 mg, 0.23 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 93 mg, 0.34 mmol), thionyl chloride (1 mL), and DIPEA (119 mg, 0.92 mmol) in THF (2 mL) to afford 85 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.11 (s, 1H), 8.69-8.67 (d, J=7.4 Hz, 1H), 8.49 (s, 1H), 8.16-8.13 (m, 2H), 7.58-7.38 (m, 5H), 4.31-4.29 (d, J=5.6 Hz, 2H), 1.55 (s, 9H), 1.12 (s, 9H); MS (m/z): 468.42 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e08bb3277241454cafd12fd152073148
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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