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Diisopropylethylamine → 4-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide

HRID 2267930
Notes
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Reaction equation

HRID 2267930 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[C:24]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:11][CH2:10]2)[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.Cl.[F:33]C1CCCNC1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#N>C(#N)CC.CCOC(C)=O>[F:33][CH:5]1[CH2:4][CH2:3][CH2:2][N:1]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[C:24]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:13][CH2:14]2)[CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27591563-FLUOROPIPERIDINE HYDROCHLORIDEHCID 589163264-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3,6-dihydro-2h-pyridin-1-yl)-ethyl]-piperidin-4-yl}-amideHCID 87175442Cyanomethyl-triphenyl phosphonium iodide

Product 1

HCID 596001974-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide

Reagents, catalysts & solvents 2

HCID 7854PropionitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 190 (see example 150) (100 mg, 0.28 mmol), 3-fluoropiperidine hydrochloride (43 mg, 0.208 mmol) and DIEA (0.189 ml, 1.12 mmol) in 0.5 ml of propionitrile is added cyanomethyl-triphenyl phosphonium iodide (81 mg, 0.336 mmol). The mixture is heated at 90° C. for 14 hours. The resulting solution is then diluted with EtOAc (20 ml) and washed twice with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product is further purified by preparative HPLC.

Workup

  1. washwashed twice with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product is further purified by preparative HPLC

Sources & evidence

ORD record
ord-06e72f0f826e4e56837c65af0d9c334c
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858781B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes