Pyridine → HCID 59395023, compound

HRID 383434Notes

Reaction equation

HRID 383434 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]([OH:14])=O)[CH2:9][NH:8][C:7]=2[CH:15]=1)#[N:2].[NH2:16][C:17]1[CH:22]=[C:21]([O:23][C:24]([O:26][CH3:27])=[O:25])[C:20]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:18]=1[CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.N1C=CC=CC=1>ClCCl>[C:42]([O:41][C:39]([N:36]1[CH2:37][CH2:38][CH:33]([C:18]2[CH:19]=[C:20]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[C:21]([O:23][C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:17]=2[NH:16][C:12]([CH:10]2[CH2:9][NH:8][C:7]3[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11]2)=[O:14])[CH2:34][CH2:35]1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 1049PyridineHCID 111923Propylphosphonic anhydrideHCID 59394991HCID 59394991, compoundHCID 59395022HCID 59395022, compound

Product 1

HCID 59395023HCID 59395023, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Cyano-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (146 mg, 0.72 mmol), tert-butyl 4-(2-amino-5-cyclopentyl-4-methoxycarbonyloxy-phenyl)piperidine-1-carboxylate (300 mg, 0.72 mmol), T3P (570 mg, 533 μL of 50% w/w solution, 1.79 mmol) were dissolved in pyridine (142 mg, 145 μL, 1.79 mmol) and dichloromethane (10 mL) and stirred for 30 min at room temperature. Purification by silica gel chromatography (10-75% ethyl acetate/hexanes) provided tert-butyl-4-[2-[(6-cyano-3,4-dihydro-2H-1,4-benzoxazine-2-carbonyl)amino]-5-cyclopentyl-4-methoxycarbonyloxy-phenyl]piperidine-1-carboxylate (333 mg, 77% yield). LC/MS m/z 605.6 [M+H]+.

Workup

  1. customPurification by silica gel chromatography (10-75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f3379741a38f4dcdaac9611c9606719e
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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