Hydrochloric Acid → HCID 25007429, compound

HRID 1015331Notes

Reaction equation

HRID 1015331 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.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.Cl.O1CCOCC1>>[ClH:29].[Cl: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

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 312751,4-DioxaneHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25007429HCID 25007429, compoundYield 56%

Procedure

The benzylamine was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (75 mg; 0.27 mmol) and 4-chlorobenzyl bromide (66 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. (66 mg; 56% yield). 1HNMR (400 MHz, DMSO-d6) δ 12.9 (s, 1H), 11.3 (s, 1H), 8.82 (s, 1H), 8.23 (s, 1H), 7.7 (m, 4H), 7.52 (d, J=6.8 Hz, 2H), 7.02 (m, 2H), 4.66 (br s, 3H), 4.26 (d, J=4.8 Hz, 2H), 4.17 (d, J=6.4 Hz, 2H), 3.34 (br d, J=11.6 Hz, 2H), 2.87 (m, 2H), 2.2 (m, 1H), 1.81 (m, 4H). MS m/z (ESI) 398 (M+H)+.

Workup

  1. filtrationSolids were filtered
  2. washrinsed once with ether

Sources & evidence

ORD record
ord-beb35977d5b449bc9d5db99ca76ced0b
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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