1-Bromopropane → HCID 25142826, compound

HRID 1677038Notes

Reaction equation

HRID 1677038 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:30][CH2:29][C:20]3[NH:21][C:22]4[C:23]([OH:28])=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2].Br[CH2:32][CH2:33][CH3:34].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([N:17]2[CH2:30][CH2:29][C:20]3[NH:21][C:22]4[C:23]([O:28][CH2:32][CH2:33][CH3:34])=[CH:24][CH:25]=[CH:26][C:27]=4[C:19]=3[CH2:18]2)=[O:16])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 11430Potassium Carbonate2×HCID 25142825HCID 25142825, compound

Product 1

HCID 25142826HCID 25142826, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(1R,2R)-2-(6-Hydroxy-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carbonyl)-cyclohexanecarboxylic acid (1-cyano-cyclopropyl)-amide (102 mg, 0.25 mmol), 1-bromopropane (28.0 uL, 0.30 mmol) and potassium carbonate (35.0 mg, 0.25 mmol) in acetone (5 mL) were heated to reflux for 3 h. Added further 1-bromopropane (58.0 uL, 0.60 mmol) and potassium carbonate (70.0 mg, 0.50 mmol) and heated overnight. The reaction darkened significantly and LCMS indicated 60% required product and 40% SM. The reaction was filtered and the liquors evaporated to dryness before redissolving in acetonitrile and purifying by preparative HPLC (0.5% HCOOH, CH3CN/H2O gradient) to give a brown glass (21.3 mg, 18%)

Workup

  1. temperatureto reflux for 3 h
  2. temperatureheated overnight

Sources & evidence

ORD record
ord-e4592e0f6ea541a5853d603b8315dd55
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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