3-(4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylpropan-1-amine → 4-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine

HRID 347492Notes

Reaction equation

HRID 347492 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:21])[C:12]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[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>>[CH3:20][N:18]([CH3:19])[CH2:17][CH2:16][CH2:15][O:14][C:12]1[C:11]([CH3:21])=[C:10]2[N:9]([CH:13]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:4][C:3]1[CH:22]=[CH:23][C:24]([NH2:26])=[CH:25][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 210815923-(4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylpropan-1-amineHCID 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 210816714-(6-(3-(Dimethylamino)propoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)-3-fluorobenzenamine

Procedure

3-(4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-N,N-dimethylpropan-1-amine (170 mg, 0.44 mmol) was converted to the title compound in a manner similar to the preparation of Compound B of Example 28. The resultant yellow solid was used in the next step without further purification. MS(ESI+) m/z 360.3 (M+H)+.

Sources & evidence

ORD record
ord-22243036e7be48559ef6e31876f5057c
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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