Trifluoroacetic acid water → HCID 67121506, compound

HRID 1423326Notes

Reaction equation

HRID 1423326 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([F:27])=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]2[N:28]([CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)[CH:29]=[C:30]([CH3:31])[C:9]=12.C(O)(C(F)(F)F)=O.O>>[F:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:16]1[CH:15]=[N:14][N:13]3[C:8]([NH2:7])=[C:9]4[C:30]([CH3:31])=[CH:29][N:28]([CH:32]5[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]5)[C:10]4=[N:11][C:12]=13)=[CH:26]2

Participants

3

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 66980243tert-butyl 4-(8-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)-7-methyl-5H-pyrazolo[1,5-a]pyrrolo[2,3-d]pyrimidin-5-yl)piperidine-1-carboxylate

Product 1

HCID 67121506HCID 67121506, compound

Procedure

At 0° C., tert-butyl 4-(8-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)-7-methyl-5H-pyrazolo[1,5-a]pyrrolo[2,3-d]pyrimidin-5-yl)piperidine-1-carboxylate (95 mg, 0.12 mmol) was treated with 80% TFA/H2O (5 mL). After stirring at room temperature for 30 min, concentration afforded crude 3-(6-fluoroquinolin-3-yl)-7-methyl-5-(piperidin-4-yl)-5H-pyrazolo[1,5-a]pyrrolo[2,3-d]pyrimidin-8-amine which was used for next step without further purification. LCMS is =0.69 Min (5 min run, UV254nm), Mass calculated for M+415.2, observed m/z 416.2 (M+H).

Workup

  1. concentrationconcentration

Sources & evidence

ORD record
ord-f8ca59a9e09f49b39e13a943b5a4ba49
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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