Hydrochloric Acid → HCID 25007781, compound

HRID 1015334Notes

Reaction equation

C(N)C1C=CC=CC=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]3)[CH2:11][CH2:10]1.[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.[ClH:38].O1CCOCC1>>[ClH:38].[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]4)[CH2:11][CH2:10]2)=[CH:32][CH:31]=1

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 7504Benzylamine

HCID 7721p-Xylyl bromide

HCID 312751,4-Dioxane

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

Product 1

HCID 25007781HCID 25007781, compoundYield 90%

Procedure

The benzylamine was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (75 mg; 0.27 mmol) and 4-methylbenzyl bromide (60 mg; 0.32 mmol) via Method BB to a solid, which was stirred in the presence of 4M HCl in dioxane (4 eq). Solids were filtered and rinsed once with ether to give title compound. (101 mg; 90% yield). 1HNMR (400 MHz, DMSO-d6) δ 12.8 (s, 1H), 11.0 (s, 1H), 8.82 (s, 1H), 8.23 (s, 1H), 7.69 (m, 2H), 7.5 (d, J=8.0 Hz, 2H), 7.25 (d, J=8.0 Hz, 2H), 4.91 (br s, 2H), 4.17 (m, 4H), 3.36 (br d, J=11.6 Hz, 2H), 2.85 (m, 2H), 2.33 (s, 3H), 2.2 (m, 1H), 1.79 (m, 4H). MS m/z (ESI) 378 (M+H)+.

Workup

filtrationSolids were filtered
washrinsed once with ether

Sources & evidence

ORD record: ord-4e8f0e1f94514af78b82118ccf7159fd
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985755B2

Reaction notes

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