3-Methylbenzoyl chloride → [4-(2,4-Diaminoquinazolin-5-yloxymethyl)piperidin-1-yl]-m-tolylmethanone

HRID 1015346Notes

Reaction equation

HRID 1015346 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[C:11]([NH2:20])=[N:12][C:13]([NH2:19])=[N:14]3)[CH2:3][CH2:2]1.[C:21]1([CH3:30])[CH:26]=[CH:25][CH:24]=[C:23]([C:27](Cl)=[O:28])[CH:22]=1>>[NH2:19][C:13]1[N:12]=[C:11]([NH2:20])[C:10]2[C:15](=[CH:16][CH:17]=[CH:18][C:9]=2[O:8][CH2:7][CH:4]2[CH2:5][CH2:6][N:1]([C:27]([C:23]3[CH:22]=[C:21]([CH3:30])[CH:26]=[CH:25][CH:24]=3)=[O:28])[CH2:2][CH2:3]2)[N:14]=1

Participants

3

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25002417[4-(2,4-Diaminoquinazolin-5-yloxymethyl)piperidin-1-yl]-m-tolylmethanoneYield 66%

Procedure

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using m-toluoyl chloride (56 mg; 0.36 mmol) via Method AA to yield 47 mg. (66% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.34 (m, 2H), 7.26 (m, 2H), 7.12 (m, 3H), 6.77 (d, J=8.0 Hz, 1H), 6.54 (d, J=8.0 Hz, 1H), 5.94 (br s, 2H), 4.53 (br s, 1H), 4.03 (d, J=6.0 Hz, 2H), 3.63 (br s, 1H), 3.08 (br s, 1H), 2.82 (br s, 1H), 2.34 (s, 3H), 2.21 (m, 1H), 1.86 (br s, 1H), 1.75 (br s, 1H), 1.31 (m, 2H). MS m/z (ESI) 392 (M+H)+.

Workup

  1. customto yield 47 mg

Sources & evidence

ORD record
ord-59858a348e7f4421a203d83ad416507c
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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