2-Methylbenzoyl chloride → HCID 25002416, compound

HRID 1015345Notes

Reaction equation

HRID 1015345 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])[C:22]([C:27](Cl)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=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:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH3:30])=[O:28])[CH2:2][CH2:3]2)[N:14]=1

Participants

3

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25002416HCID 25002416, compoundYield 70%

Procedure

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using o-toluoyl chloride (57 mg; 0.37 mmol) via Method AA to yield 101 mg. (70% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.35 (t, J=8.4 Hz, 1H), 7.25 (m, 6H), 6.76 (d, J=8.0 Hz, 1H), 6.54 (d, J=8.0 Hz, 1H), 5.94 (br s, 2H), 4.59 (br d, J=13.2 Hz, 1H), 4.03 (d, J=6.0 Hz, 2H), 3.3 (m, 1H), 3.04 (t, J=11.6 Hz, 1H), 2.88 (t, J=12.0 Hz, 1H), 2.23 (m, 4H), 1.89 (br d, J=13.2 Hz, 1H), 1.69 (m, 1H), 1.24 (m, 2H). MS m/z (ESI) 392 (M+H)+.

Workup

  1. customto yield 101 mg

Sources & evidence

ORD record
ord-28ce12e27a1c4901b0a78f0403b22218
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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