tert-butyl (3S)-3-aminopiperidine-1-carboxylate → HCID 58710594, compound

HRID 646761Notes

Reaction equation

HRID 646761 reaction equation
CO[C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][CH:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH:21]3[OH:29])[CH:13]=2)[N:6]=1)=[O:4].[NH2:30][C@H:31]1[CH2:36][CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]1>O>[NH2:11][C:10]1[C:5]([C:3]([NH:30][C@H:31]2[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]2)=[O:4])=[N:6][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][C@@H:21]3[OH:29])[CH:13]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 68650629HCID 68650629, compound

Product 1

HCID 58710594HCID 58710594, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-6-{3-[(2-hydroxy-indan-1-ylamino)-methyl]-phenyl}-pyrazine-2-carboxylic acid methyl ester (400.0 mg, 1.02 mmol) and 1,1-dimethylethyl (3S)-3-aminopiperidine-1-carboxylate (970.0 mg, 4.84 mmol) was heated to 120° C. overnight. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate (2×50 mL) then dried over anhydrous sodium sulfate and filteration, concentration and purified by column chromatography (3% MeOH/Dichloromethane) and subsequently it was treated with 4.0 M HCl in dioxane (20 mL) to give 3-amino-6-[3-({[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}methyl)phenyl]-N-[(3S)-piperidin-3-yl]pyrazine-2-carboxamide, 275.0 mg (58.7% yield). 1H NMR (400 MHz, d4-MeOH): δ 8.72 (s, 2H), 8.18 (s, 1H), 7.80 (d, 1H), 7.60 (m, 2H), 7.38 (m, 3H), 4.80 (s, 1H), 4.50(s, 2H), 4.40 (m, 1H), 3.65 (m, 2H), 3.42 (m, 5H), 3.16 (m, 2H), 2.15 (m, 2H), 1.87 (m, 1H); MS (EI) for C26H30N6O2: 459.31 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
  3. custompurified by column chromatography (3% MeOH/Dichloromethane) and subsequently it
  4. additionwas treated with 4.0 M HCl in dioxane (20 mL)

Sources & evidence

ORD record
ord-3e195acc95824f08ae1dd7ccc873ea98
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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