Diisopropylethylamine → HCID 178511085, compound

HRID 711973Notes

Reaction equation

HRID 711973 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH:11]=[CH:12][S:13][C:3]=12.OC(C(F)(F)F)=O.[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][C:29]#[N:30])[CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[N+:8]([C:7]1[C:2]([NH:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([CH2:28][C:29]#[N:30])[CH2:24][CH2:23]2)=[C:3]2[S:13][CH:12]=[CH:11][C:4]2=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineHCID 178511087HCID 178511087, compound

Product 1

HCID 178511085HCID 178511085, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.88 g, 4.1 mmol) in isopropyl alcohol (14 mL), (trans-4-aminocyclohexyl)acetonitrile TFA salt (0.68 g, 4.9 mmol) and N,N-diisopropylethylamine (3.0 mL, 17 mmol) were added. The reaction was stirred at 90° C. for 2 h. The mixture was concentrated and purified on silica gel (eluting with 0 to 60% EtOAc in dichloromethane) to give the desired product (1 g, 77%). LCMS calculated for C15H17N4O2S (M+H)+: m/z=317.1. Found: 317.0.

Workup

  1. additionwere added
  2. concentrationThe mixture was concentrated
  3. custompurified on silica gel (eluting with 0 to 60% EtOAc in dichloromethane)

Sources & evidence

ORD record
ord-fdd4d2d1ec9a4c49813c06bfd0568d23
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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