4-Amino-2,2,6,6-tetramethylpiperidine → HCID 86761155, compound

HRID 504154Notes

Reaction equation

HRID 504154 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([NH:19][C@@H:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][F:35])=[CH:27][CH:26]=2)[C:21]([OH:23])=O)=[O:18])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:36][CH:37]1[CH2:42][C:41]([CH3:44])([CH3:43])[NH:40][C:39]([CH3:46])([CH3:45])[CH2:38]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[F:35][CH2:34][CH2:33][CH2:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C@H:20]([NH:19][C:17]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][N:11]2[S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)(=[O:10])=[O:9])=[O:18])[C:21](=[O:23])[NH:36][CH:37]2[CH2:38][C:39]([CH3:46])([CH3:45])[NH:40][C:41]([CH3:44])([CH3:43])[CH2:42]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66750594HCID 66750594, compound

Product 1

HCID 86761155HCID 86761155, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-{[(S)-1-(3-Fluoro-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-[4-(3-fluoro-propoxy)-phenyl]-propionic acid (80 mg, 0.16 mmol), 4-amino-2,2,6,6-tetramethylpiperidine (25 mg, 0.16 mmol), 1-hydroxybenzotriazole (30 mg, 0.22 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (39 mg, 0.20 mmol) were mixed in dichloromethane (2 mL). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed twice with a saturated aqueous sodium bicarbonate solution, and the organic fraction dried over magnesium sulfate. After filtration and subsequent concentration, the resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel to produce 27 mg (27%) of the title compound. MS: m/e 649.33 (M+H). 1H NMR (300 MHz, d6-DMSO): δ0.70-2.20 (m, 27H), 2.80 (m, 2H), 3.20 (m, 1H), 3.65 (d, 1H, J=12 Hz), 4.00 (m, 3H), 4.30 (q, 1H, J=6 Hz), 4.50 (m, 2H), 4.65 (t, 1H, J=6 Hz), 6.90 (d, 2H, J=9 Hz), 7.15 (d, 2H, J=9 Hz), 7.50 (m, 4H), 8.00 (m, 2H).

Workup

  1. washwashed twice with a saturated aqueous sodium bicarbonate solution
  2. dry with materialthe organic fraction dried over magnesium sulfate
  3. filtrationAfter filtration and subsequent concentration
  4. customthe resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel

Sources & evidence

ORD record
ord-ffa7b507f4014bf48fa19b1242ad90a9
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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