Hydrochloric Acid → (S)-2-(1-Aminoethyl)-5-(6-(4-isopropylpiperazin-1-yl)-6-oxohex-1-yn-1-yl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052501Notes

Reaction equation

HRID 1052501 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:42])[CH2:11][CH2:12][CH2:13][C:14]#[C:15][C:16]2[CH:17]=[CH:18][N:19]3[C:24]=2[C:23](=[O:25])[N:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([C@@H:32]([NH:34]C(=O)OC(C)(C)C)[CH3:33])=[N:20]3)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl>>[NH2:34][C@H:32]([C:21]1[N:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:25])[C:24]2=[C:16]([C:15]#[C:14][CH2:13][CH2:12][CH2:11][C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]3)=[O:42])[CH:17]=[CH:18][N:19]2[N:20]=1)[CH3:33]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131736173(S)-tert-Butyl (1-(5-(6-(4-isopropylpiperazin-1-yl)-6-oxohex-1-yn-1-yl)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 118433984(S)-2-(1-Aminoethyl)-5-(6-(4-isopropylpiperazin-1-yl)-6-oxohex-1-yn-1-yl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Procedure

(S)-tert-Butyl (1-(5-(6-(4-isopropylpiperazin-1-yl)-6-oxohex-1-yn-1-yl)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (134 mg, 0.23 mmol) was dissolved in hydrogen chloride (4M in dioxane, 2.5 ml, 10 mmol) and stirred at room temperature overnight. The solvent was removed and tert-butanol and DIEA were added to the crude and the reaction mixture was stirred at 120° C. overnight. The solvents were removed and this crude was used in the following step without further purification. Purity 10%

Workup

  1. customThe solvent was removed
  2. additiontert-butanol and DIEA were added to the crude
  3. stirringthe reaction mixture was stirred at 120° C. overnight
  4. customThe solvents were removed
  5. customthis crude was used in the following step without further purification

Sources & evidence

ORD record
ord-a898b3282f854df2a9665b4a1f4c4387
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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