Ethylorthoformate → HCID 178420025, compound

HRID 707302Notes

Reaction equation

HRID 707302 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12]1.[CH:23]([O-])([O-])OCC>C(O)(=O)C>[N:22]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C@H:13]2[CH2:12][C@H:11]([NH:10][C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH2:14]2)[CH:23]=1

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 178507706HCID 178507706, compound

Product 1

HCID 178420025HCID 178420025, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

N2-(Trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)pyridine-2,3-diamine (intermediate from step 3 in example 1, 0.100 g, 0.321 mmol) was dissolved in acetic acid (10 mL) and treated with ethyl orthoformate (2.0 ml, 12.02 mmol). The solution was heated at 90° C. for 20 minutes and the solution evaporated to dryness under reduced pressure. Purification using the silica chromatography (0-10% methanol in dichloromethane gradient) gave the desired N-(trans-3-(3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)benzo[d]thiazol-2-amine (0.061 g, 0.190 mmol, 59.1% yield) as an off-white solid. M+1: 322.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.82 (ddd, J=13.89, 8.51, 4.01 Hz, 2 H) 3.20-3.32 (m, 2 H) 4.61 (tt, J=7.73, 4.01 Hz, 1 H) 5.37 (quin, J=7.68 Hz, 1 H) 7.06-7.15 (m, 1 H) 7.23-7.34 (m, 2 H) 7.61 (d, J=8.02 Hz, 1 H) 7.58 (d, J=8.22 Hz, 1 H) 8.10 (dd, J=8.12, 1.27 Hz, 1 H) 8.19 (s, 1 H) 8.41 (dd, J=4.69, 1.37 Hz, 1 H).

Workup

  1. customthe solution evaporated to dryness under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-832204b2c8f647c09e21049c54503f30
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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