Carbonate Ion → HCID 66811685, compound

HRID 1099214Notes

Reaction equation

HRID 1099214 reaction equation
[NH:1]([C:3]([C:5]1[CH:10]=[C:9]([N:11]([CH3:17])[CH2:12][C@@H:13]2[CH2:15][C@H:14]2[CH3:16])[N:8]=[C:7]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=1)=[O:4])[NH2:2].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:32]1[C:43](O)=[O:44])=[O:30])([CH3:27])([CH3:26])[CH3:25].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-]>ClCCCl>[CH3:17][N:11]([CH2:12][C@@H:13]1[CH2:15][C@H:14]1[CH3:16])[C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[N:8]=1)[C:3]([NH:1][NH:2][C:43]([C@H:32]1[C@@H:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:34][CH2:35][CH2:36][N:31]1[C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])=[O:44])=[O:4]

Participants

7

Reactant 5

HCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66811207HCID 66811207, compound2×HCID 66811655HCID 66811655, compound

Product 1

HCID 66811685HCID 66811685, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-[4-(hydrazinocarbonyl)-6-(methyl[(trans-2-methylcyclopropyl)methyl]amino)pyridin-2-yl]-N-methylmethanesulfonamide (3A.3b-1, 59.0 mg, 0.17 mmol) in 1,2-dichloroethane (2 ml) were added cis-1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (Intermediate 1A.5, 45.9 mg, 0.15 mmol), 1-hydroxybenzotriazole (23.2 mg, 0.16 mmol), diisopropylethylamine (0.090 ml, 0.52 mmol), and polystyrene bound carbodiimide (246 mg, 0.34 mmol, 1.31 mmol/g). The reaction mixture was allowed to stir gently at room temperature for 18 h. Macroporous carbonate resin (360 mg, 0.68 mmol, 2.74 mmol/g) was added to the reaction, and the mixture was again allowed to stir gently for 18 h. The reaction mixture was filtered and concentrated in vacuo to yield tert-butyl cis-2-[(2-{2-(methyl[(trans-2-methylcyclopropyl)methyl]amino)-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazino)carbonyl]-3-phenylpiperidine-1-carboxylate.

Workup

  1. stirringto stir gently for 18 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c25f6d23d15c464cbd1264d04a1de57a
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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