Cyclohexanemethanol → HCID 44159222, compound

HRID 517871Notes

Reaction equation

HRID 517871 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]3[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18][C:5]=3[C:4]=2[CH:3]=1.[CH:20]1([CH2:26]O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([O:14][CH2:26][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:13])[C:6]3[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 7507CyclohexanemethanolHCID 10868DicyclohexylcarbodiimideHCID 59161636HCID 59161636, compound

Product 1

HCID 44159222HCID 44159222, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetic acid (200 mg, 0.7 mmol) and cyclohexyl methanol (80 mg, 0.7 mmol) in dichloromethane (10 ml) were added N,N′-dicyclohexylcarbodiimide (177 mg, 0.86 mmol) and 4-dimethylaminopyridine (105 mg, 0.86 mmol) and the contents were stirred at 25 deg C. for 16 h. The reaction mixture was concentrated to dryness to obtain the crude compound which was purified by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 ml) to give 30 mg (11.3%) of cyclohexylmethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate as TFA salt. 1H NMR (DMSO) TFA SALT 10.39 (bs, 1H), 7.60 (s, 1H), 7.50 (d, 1H), 7.2 (d, 1H), 5.3-5.1 (dd, 2H), 4.70 (d, 1H), 4.30 (bs, 1H), 4.0 (d, 2H), 3.85 (bs, 1H), 3.50 (bs, 1H), 3.10 (s, 2H), 2.85 (s, 3H), 1.60-0.90 (m, 11H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customto obtain the crude compound which
  3. customwas purified by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 ml)

Sources & evidence

ORD record
ord-4825afd5c2ef431897711e2413fb7844
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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