Formaldehyde → 5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531772Notes

Reaction equation

HRID 531772 reaction equation
Cl.F[C:3]1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCNCC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[CH2:46]([N:54]1[CH:58]=[C:57]([C:59]2[C:67]3[C:62](=[N:63][CH:64]=[C:65]([C:68]4[CH:69]=[N:70][C:71]([N:74]5[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]5)=[CH:72][CH:73]=4)[CH:66]=3)[N:61]([S:80]([C:83]3[CH:89]=[CH:88][C:86]([CH3:87])=[CH:85][CH:84]=3)(=[O:82])=[O:81])[CH:60]=2)[CH:56]=[N:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH3:3][N:77]1[CH2:78][CH2:79][N:74]([C:71]2[N:70]=[CH:69][C:68]([C:65]3[CH:66]=[C:67]4[C:59]([C:57]5[CH:56]=[N:55][N:54]([CH2:46][CH2:47][C:48]6[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=6)[CH:58]=5)=[CH:60][N:61]([S:80]([C:83]5[CH:84]=[CH:85][C:86]([CH3:87])=[CH:88][CH:89]=5)(=[O:81])=[O:82])[C:62]4=[N:63][CH:64]=3)=[CH:73][CH:72]=2)[CH2:75][CH2:76]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 900313493-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 900315215-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-133, 3-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (product of step 2 of example 140) (50 mg, 0.082 mmol) was methylated using paraformaldehyde (8 mg, 0.24 mmol) and Na(OAc)3BH (35 mg, 0.164 mmol) in dichloroethane (10 mL) to afford 50 mg (99% yield) of the titled compound. MS: m/z=618.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-65dce79f038142e98feda3c3d38e23bd
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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