Hydrochloric Acid → 5-[1-(2,4-Difluorobenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine hydrochloride

HRID 1015335Notes

Reaction equation

HRID 1015335 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.[F:29][C:30]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:31]=1[CH2:32][Cl:33].Cl>O1CCOCC1>[ClH:33].[F:29][C:30]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:31]=1[CH2:32][N: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

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 27369481-(Chloromethyl)-2,4-difluorobenzeneHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 250077835-[1-(2,4-Difluorobenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The benzylamine was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (75 mg; 0.27 mmol) and 2,4-difluorobenzyl chloride (69 mg; 0.35 mmol) via Method BB. Solids were suspended in 2 mL dioxane and 0.5 mL 4M HCl in dioxane was added and after 2 hours stirring at room temperature solids were collected by filtration to yield 92 mg. (78% yield). 1HNMR (400 MHz, DMSO-d6) δ 12.8 (s, 1H), 11.2 (s, 1H), 8.84 (s, 1H), 8.23 (s, 1H), 7.88 (q, J=8.8, 6.4 Hz, 1H), 7.7 (m, 2H), 7.4 (m, 1H), 7.23 (m, 1H), 7.02 (m, 2H), 4.28 (d, J=4.4 Hz, 2H), 4.17 (d, J=6.4 Hz, 2H), 3.4 (br d, J=11.6 Hz, 2H), 2.95 (m, 2H), 2.23 (m, 1H), 1.81 (d, J=13.2 Hz, 2H), 1.73 (m, 2H). MS m/z (ESI) 400 (M+H)+.

Workup

  1. filtrationwere collected by filtration
  2. customto yield 92 mg

Sources & evidence

ORD record
ord-ce8ef275db1242e2a039b8cd76aa34c6
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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