Trifluoroacetic acid → HCID 22390473, compound

HRID 1072087Notes

Reaction equation

HRID 1072087 reaction equation
C(OC(N1CCC(NCC2C=CN3C=2C(NC2C=C4C(=CC=2)N(CC2C=CC=C(F)C=2)N=C4)=NC=N3)CC1)=O)(C)(C)C.C(OC([N:50]1[CH2:55][CH2:54][CH:53]([N:56]([CH2:58][C:59]2[CH:60]=[CH:61][N:62]3[C:67]=2[C:66]([NH:68][C:69]2[CH:70]=[C:71]4[C:75](=[CH:76][CH:77]=2)[N:74]([CH2:78][C:79]2[CH:84]=[CH:83][CH:82]=[C:81]([F:85])[CH:80]=2)[N:73]=[CH:72]4)=[N:65][CH:64]=[N:63]3)[CH3:57])[CH2:52][CH2:51]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[F:85][C:81]1[CH:80]=[C:79]([CH:84]=[CH:83][CH:82]=1)[CH2:78][N:74]1[C:75]2[C:71](=[CH:70][C:69]([NH:68][C:66]3[C:67]4=[C:59]([CH2:58][N:56]([CH3:57])[CH:53]5[CH2:52][CH2:51][NH:50][CH2:55][CH2:54]5)[CH:60]=[CH:61][N:62]4[N:63]=[CH:64][N:65]=3)=[CH:77][CH:76]=2)[CH:72]=[N:73]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67412000HCID 67412000, compoundHCID 67413490HCID 67413490, compound

Product 1

HCID 22390473HCID 22390473, compoundYield 37%

Procedure

Similarly, 4-({4-[1-(3-fluoro-benzyl)-1H-indazol-5ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-amino)-piperidin-1-carboxylic acid tert-butyl ester was convertet to 4-({4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-methylamino)-piperidin-1-carboxylic acid tert-butyl ester which was treated with TFA at 0° C. for 1 h to give the title compound as a solid (overall yield 37%). MS: 485 (M+H)+; HPLC Ret Time: 0.95 min (YMC 3.0×50 mm S7 C18 column, 2 min gradient, 5 ml/min).

Sources & evidence

ORD record
ord-b91a765d288f486cb6cd98be867da692
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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