2-(4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylethanamine → 4-(6-(2-(Dimethylamino)ethoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine

HRID 347494Notes

Reaction equation

HRID 347494 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:20])[C:12]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.Cl.Cl.FC1C=C(NC(NC(=O)CC2C=CC(F)=CC=2)=S)C=CC=1OC1C2=C(C)C(OCCN3CCN(C)CC3)=CN2N=CN=1>>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][O:14][C:12]1[C:11]([CH3:20])=[C:10]2[N:9]([CH:13]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:4][C:3]1[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 210815432-(4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylethanamineHCID 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 210816704-(6-(2-(Dimethylamino)ethoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamineYield 100%

Procedure

2-(4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylethanamine (22 mg, 0.06 mmol) was converted to the title compound (20 mg, 100%) in a manner similar to the preparation of Compound B of Example 28. The resultant yellow glass was used in the next step without further purification. MS(ESI+) m/z 346.3 (M+H)+.

Sources & evidence

ORD record
ord-618b0cb496474bc2864b159be35e2c5d
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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