2-Naphthoyl chloride → HCID 25002415, compound

HRID 1015344Notes

Reaction equation

HRID 1015344 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.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[C:31](Cl)=[O:32]>>[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:31]([C:22]3[CH:23]=[CH:24][C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=3)=[O:32])[CH2:2][CH2:3]2)[N:14]=1

Participants

3

Reactant 2

HCID 752462-Naphthoyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25002415HCID 25002415, compoundYield 88%

Procedure

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using 2-naphthoyl chloride (70.5 mg; 0.37 mmol) via Method AA to yield 139 mg. (88% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.97 (m, 4H), 7.58 (m, 2H), 7.50 (dd, J=8.4, 1.6 Hz, 1H), 7.35 (t, J=8.4 Hz, 1H), 7.2 (br s, 2H), 6.76 (d, J=8.0 Hz, 1H), 6.55 (d, J=8.0 Hz, 1H), 5.94 (br s, 2H), 4.59 (br s, 1H), 4.04 (d, J=6.0 Hz, 2H), 3.72 (br s, 1H), 3.15 (br s, 1H), 2.91 (br s, 1H), 2.24 (m, 1H), 1.9 (br s, 1H), 1.75 (br s, 1H), 1.35 (m, 2H). MS m/z (ESI) 428 (M+H)+.

Workup

  1. customto yield 139 mg

Sources & evidence

ORD record
ord-3632213ebf5f44b6985552d2b47d850d
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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