Diisopropylethylamine → HCID 178474991, compound

HRID 518753Notes

Reaction equation

HRID 518753 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:12])[CH3:11])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.F[C:23]1[CH:24]=[C:25]([CH2:32][OH:33])[CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30]>C(#N)C>[OH:33][CH2:32][C:25]1[CH:26]=[CH:27][C:28]([N+:29]([O-:31])=[O:30])=[C:23]([NH:2][C@H:3]2[CH2:4][CH2:5][C@H:6]([NH:9][C:10](=[O:12])[CH3:11])[CH2:7][CH2:8]2)[CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27746583-Fluoro-4-nitrobenzyl alcoholHCID 178474995HCID 178474995, compound

Product 1

HCID 178474991HCID 178474991, compoundYield 17.24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-(trans-4-aminocyclohexyl)acetamide hydrochloride (200 mg, 1.038 mmol) and DIPEA (0.494 mL, 2.83 mmol) in ACN (2 mL) was added (3-fluoro-4-nitrophenyl)methanol (161 mg, 0.944 mmol). The resulting mixture was stirred overnight at 80° C. After 16 hours, the reaction was concentrated and the residue purified by column chromatography, eluting with 0-10% MeOH in DCM, to provide N-(trans-4-(5-(hydroxymethyl)-2-nitrophenylamino)cyclohexyl)acetamide as a yellow powder (50 mg, 17.24% yield). MS, m/z (C15H21N3O4): calcd, 307.2. found, 308.1 [M+H].

Workup

  1. waitAfter 16 hours
  2. concentrationthe reaction was concentrated
  3. customthe residue purified by column chromatography
  4. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-4caa372f18fa4551af1b264dfbaf3456
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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