Cyclohexylamine → HCID 86717445, compound

HRID 711981Notes

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.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH:14]1([NH:20][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[CH:11]=[CH:12][S:13][C:3]=23)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.055 g, 0.26 mmol) (Example 1, Step 2), cyclohexanamine (59 μL, 0.51 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.77 mmol) in isopropyl alcohol (0.87 mL) was heated at 90° C. for 2 h. The resulting mixture was concentrated to give the desired product, which was used directly in the next step. LCMS calculated for C13H16N3O2S (M+H)+: m/z=278.1. Found: 278.0.

Workup

concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record: ord-7ed188127f9d4a0ba5689e8aabd17073
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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