4-(2-Fluoro-4-(3-(2-(4-fluorophenyl)acetyl)ureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate → 1-(4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea, hydrochloride salt

HRID 347493Notes

Reaction equation

HRID 347493 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:25])=[C:9]2[N:14]([CH:15]=1)[N:13]=[CH:12][N:11]=[C:10]2[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[F:24].[ClH:27].Cl.FC1C=C(NC(NC(=O)CC2C=CC(F)=CC=2)=S)C=CC=1OC1C2=C(C)C(OCCN3CCN(C)CC3)=CN2N=CN=1.C(NC(=O)OC1C(C)=C2N(C=1)N=CN=C2OC1C=CC(N[C:93]([NH:95][C:96](=[O:105])[CH2:97][C:98]2[CH:103]=[CH:102][C:101]([F:104])=[CH:100][CH:99]=2)=[O:94])=CC=1F)C>>[ClH:27].[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:25])=[C:9]2[N:14]([CH:15]=1)[N:13]=[CH:12][N:11]=[C:10]2[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:93]([NH:95][C:96](=[O:105])[CH2:97][C:98]2[CH:103]=[CH:102][C:101]([F:104])=[CH:100][CH:99]=2)=[O:94])=[CH:19][C:18]=1[F:24]

Participants

4

Reactant 3

HCID 114973464-(2-Fluoro-4-(3-(2-(4-fluorophenyl)acetyl)ureido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate2×HCID 210816714-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamineHCID 1317262361-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4] triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea, bis-hydrochloride salt

Product 1

HCID 1317262371-(4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea, hydrochloride saltYield 13%

Procedure

4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine (12 mg, 0.03 mmol) was converted to the title compound (2.5 mg, 13%) in a manner similar to the preparation of Compound E of Example 31, except that 2-(4-fluorophenyl)-acetyl isocyanate (0.10 mL, 0.04 mmol, Compound C of Example 4) was used instead of benzenesulfonyl isocyanate. 1H NMR (CD3OD) δ 10.77 (s, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.40–7.23 (m, 5H), 7.11–7.02 (m, 3 H), 4.15–4.12 (m, 2H), 3.71 (s, 2H), 3.41–3.36 (m, 2H), 2.97 (s, 6H), 2.44 (s, 3H), 2.31–2.22 (m, 2H); HRMS(ESI), 539.2218 (M+H)+ calc, 539.2218 (M+H)+ found.

Sources & evidence

ORD record
ord-51f6f6caf0b54d16a1db601f9700db44
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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