Diisopropylethylamine → tert-Butyl-4-(1-{[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}-2-methoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 2093656Notes

Reaction equation

HRID 2093656 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:21]([CH3:23])[CH3:22])[C:6]2[O:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:20]=1)#[N:2].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH:37]([NH2:42])[C:38]([O:40][CH3:41])=[O:39])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH:37]([NH:42][C:15](=[O:16])[C:14]2[CH:13]=[CH:12][C:11]([C:9]3[O:10][C:6]4[C:5]([CH:21]([CH3:23])[CH3:22])=[CH:4][C:3]([C:1]#[N:2])=[CH:20][C:7]=4[N:8]=3)=[CH:19][CH:18]=2)[C:38]([O:40][CH3:41])=[O:39])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 24729638Tert-butyl 4-(1-amino-2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 573699454-(5-Cyano-7-isopropylbenzo[d]oxazol-2-yl)benzoic acid2×

Product 1

HCID 68744285tert-Butyl-4-(1-{[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}-2-methoxy-2-oxoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, a 2-dram vial equipped with a magnetic stirrer was charged with 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoic acid (INTERMEDIATE 2), 4-(amino-methoxycarbonyl-methyl)-piperidine-1-carboxylic acid tert-butyl ester, bromo-tris-pyrrolidino phosphonium hexafluorophosphate, and dimethylformamide (5 ml). To this mixture was added of N,N-diisopropylethylamine, dropwise. The reaction mixture was allowed to stir at room temperature for 3 d. The residue was purified by flash chromatography using a Biotage SP 1, 40M silica cartridge, eluting with a linear gradient of 20% to 100% hexanes in ethyl acetate over 15 column volumes to provide the title compound. Mass spectrum (ESI) 559.3 (M+1).

Workup

  1. customAt room temperature, a 2-dram vial equipped with a magnetic stirrer
  2. customThe residue was purified by flash chromatography
  3. washeluting with a linear gradient of 20% to 100% hexanes in ethyl acetate over 15 column volumes

Sources & evidence

ORD record
ord-d047a0053d174b5f852fc6a65d59535d
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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