Trifluoroacetic acid → HCID 58382104, compound

HRID 1628116Notes

Reaction equation

HRID 1628116 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:35]([CH2:36][O:37]CC[Si](C)(C)C)[C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:21]([CH2:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[N:22][CH:23]=3)[C:15]=2[CH:14]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][CH2:26][CH2:25][CH2:24][C:21]1[N:20]2[C:15]3[CH:14]=[C:13]([C:6]4[C:5]5[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=5)[N:8]([CH3:12])[CH:7]=4)[N:35]([CH2:36][OH:37])[C:16]=3[N:17]=[CH:18][C:19]2=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58382389HCID 58382389, compound

Product 1

HCID 58382104HCID 58382104, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propylcarbamate (0.347 g, 0.574 mmol, prepared using J.1 from Preparation #I.1 with 4-(tert-butoxycarbonylamino)butyric acid and L.1 with mercury(II) trifluoroacetate) in DCM (5 mL) at rt was added TFA (1.10 mL, 14.3 mmol). After about 16 h, the mixture was concentrated in vacuo to provide (1-(3-aminopropyl)-7-(5-methoxy-1-methyl-1H-indol-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-6-yl)-methanol (0.232 g, 100%): LC/MS (Table 2, Method c) Rt=1.26 min; MS m/z 405 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-788b1450f07d47adad81aebc72433017
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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