Dichloromethane → HCID 71253494, compound

HRID 1775062Notes

Reaction equation

HRID 1775062 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[N:14][N:13](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:10]3=[CH:11][N:12]=2)[CH:2]=1.C(Cl)Cl.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20]4)=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:2]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 71253915HCID 71253915, compound

Product 1

HCID 71253494HCID 71253494, compoundYield 35.8%

Procedure

To a solution of 5-(pyridin-3-yl)-3-(pyrrolidin-1-yl)-1-trityl-1H-pyrazolo[3,4-c]pyridine (0.120 g, 0.236 mmol) in Methylene chloride (3.030 mL, 47.28 mmol) was added Triethylsilane (0.151 mL, 0.946 mmol) and Trifluoroacetic Acid (3.642 mL, 47.28 mmol). The mixture was stirred at RT for 3 h. The reaction was concentrated. The crude was submitted for HPLC purification in DMF to give 252 (22.4 mg, 35.7% yield). ESI MS m/z=266.1 (M+1). 1H NMR (400 MHz, DMSO) δ 12.34 (s, 1H), 9.30 (d, J=1.8 Hz, 1H), 8.90 (d, J=0.9 Hz, 1H), 8.53 (dd, J=4.7, 1.5 Hz, 1H), 8.50-8.42 (m, 1H), 8.32 (s, 1H), 7.47 (dd, J=7.9, 4.7 Hz, 1H), 3.63 (t, J=6.5 Hz, 4H), 1.99 (t, J=6.5 Hz, 4H)

Workup

  1. concentrationThe reaction was concentrated
  2. customThe crude was submitted for HPLC purification in DMF

Sources & evidence

ORD record
ord-cf9db2b7009c4dfb939293b1bcec94d7
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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