Dimethylamine → N-{4-[(3-iodophenyl)amino]quinazoline-6-yl}-4-(dimethylamino)-2-butenamide

HRID 346420Notes

Reaction equation

HRID 346420 reaction equation
[I: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.Br/C(=C\C)/C(O)=O.CNC.ClC1C=C(NC2C3C(=CC=C(N[C:51](=[O:58])[CH:52]=[CH:53][CH2:54][N:55]([CH3:57])[CH3:56])C=3)N=CN=2)C(F)=CC=1Cl>>[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:51](=[O:58])[CH:52]=[CH:53][CH2:54][N:55]([CH3:57])[CH3:56])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 53129522-Bromo-2-Butenoic AcidHCID 210800024-[(3-Iodophenyl)amino]-6-aminoquinazolineHCID 68564223N-{4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl}-4-(dimethylamino)-2-butenamide

Product 1

HCID 68562749N-{4-[(3-iodophenyl)amino]quinazoline-6-yl}-4-(dimethylamino)-2-butenamide

Procedure

A solution of 4-[(3-iodophenyl)amino]-6-aminoquinazoline was reacted with bromocrotonic acid and dimethylamine, as is described hereinabove in Compound 4, to give N-{4-[(3-iodophenyl)amino]quinazoline-6-yl}-4-(dimethylamino)-2-butenamide. MS (m/z): 465 (M+H)+, 509 (M+)+; 1H-NMR (DMSO-d6): δ=4.38 (d, 1H), 4.49 (d, 1H), 6.5 (dd, 1H), 6.94 (dt, 1H), 7.19 (t, 1H), 7.47 (d, 1H), 7.85 (mt, 3H), 8.27 (s, 1H), 8.58 (s, 1H), 8.82 (s, 1H) 10.59 (s, 1H); Anal. Calc: C, 42.46; H, 2.77; N, 11.0. Found: C, 46.52; H, 3.04; N, 12.06. HPLC analysis: C-18 column, 55% acetate buffer/45% acetonitrile, flow=1.0 ml/min; r.t.=26.55 minutes (first peak), 29.99 minutes (second peak).

Sources & evidence

ORD record
ord-102cdf3caf2446aabdf75ff2473d3f1d
Source dataset
uspto-grants-2007_02
Patent number
US07172749B2

Reaction notes

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