Hydrochloric Acid → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57882Notes

Reaction equation

HRID 57882 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[N:12]=[CH:11][C:10]3[CH:13]=[N:14][N:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)[CH:19]=[CH:18][CH:17]=4)[C:9]=3[CH:8]=2)[CH:4]=[N:3][CH:2]=1.Cl>CO>[N:22]1([C:20]2[N:21]=[C:16]([N:15]3[C:9]4[CH:8]=[C:7]([C:5]5[CH:4]=[N:3][CH:2]=[N:1][CH:6]=5)[N:12]=[CH:11][C:10]=4[CH:13]=[N:14]3)[CH:17]=[CH:18][CH:19]=2)[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707075tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 867070761-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (320 mg, 0.68 mmol) in a solution of HCl in MeOH (3.0 N, 20 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by prepared HPLC to afford 175 as a light yellow solid (220 mg, yield 87%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.43 (s, 1H), 9.39 (s, 1H), 9.35 (d, J=3.0 Hz, 1H), 9.28 (d, J=3.0 Hz, 1H), 9.06 (d, J=11.5 Hz, 1H), 8.66 (d, J=5.5 Hz, 1H), 7.70 (dd, J=8.0 and 16.5 Hz, 1H), 7.17 (dd, J=7.5 and 11.0 Hz, 1H), 6.61 (t, J=8.0 Hz, 1H), 3.83 (s, 2H), 3.77 (s, 2H), 3.56 (m, 1H), 2.95 (t, J=5.0 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 1.84 (t, J=5.0 Hz, 2H). ESI (MS) m/z: 373 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified
  3. customby prepared HPLC

Sources & evidence

ORD record
ord-8869e3e72a1142489f5e4048b4408284
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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