Dimethylamine → HCID 44629538, compound

HRID 1520728Notes

Reaction equation

HRID 1520728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].[CH3:27][NH:28][CH3:29].CO>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][N:28]([CH3:29])[CH3:27])[CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 783704-Chlorobutyryl chlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 44629538HCID 44629538, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of N4-(3-bromophenyl)-4,6-quinazolinediamine (10) (1.76 g, 5.58 mmol) with 4-chlorobutanoyl chloride (0.75 mL, 6.70 mmol) and then aqueous dimethylamine according to the general procedure A, with the exception that the first step was performed in dioxane and the second at 50° C. for 24 hours, gave N-[4-(3-bromoanilino)-6-quinazolinyl]-4-(dimethylamino)butanamide (16) (36%) as a white solid, m.p. (MeOH) 180-182° C. 1H NMR [(CD3)2SO] δ 10.23 (s, 1H), 9.87 (s, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.57 (s, 1H), 8.17 (dd, J=1.9, 1.9 Hz, 1H), 7.88-7.84 (m, 2H), 7.77 (d, J=8.9 Hz, 1H), 7.37-7.27 (m, 2H), 2.43 (t, J=7.2 Hz, 2H), 2.29 (t, J=7.2 Hz, 2H), 2.16 (s, 6H), 1.78 (quintet, J=7.2 Hz, 2H). Analysis found: C, 55.46; H, 5.33; N, 15.96. C20H22BrN5O.¼H2O requires: C, 55.50; H, 5.24; N, 16.18.

Sources & evidence

ORD record
ord-a7b89e2b0d5643e2926f022789907585
Source dataset
uspto-grants-2015_07
Patent number
US09073916B2

Reaction notes

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