Diisopropylethylamine → Tert-butyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)benzoate

HRID 1410010Notes

Reaction equation

HRID 1410010 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24](O)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:30]([O:34][C:35](=[O:43])[C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)([CH3:33])([CH3:32])[CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:42][C:39]4[CH:38]=[CH:37][C:36]([C:35]([O:34][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:43])=[CH:41][CH:40]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 683795141-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid

Product 1

HCID 68379721Tert-butyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)benzoateYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (57 mg, 0.137 mmol), tert-butyl-4-aminobenzoate (34.4 mg, 0.178 mmol), HATU (67.6 mg, 0.178 mmol) and DIEA (53 mg, 0.411 mmol) in 10 mL of DMF was stirred at room temperature for 72 hours. The solvent was evaporated and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, ethyl acetate:petroleum ether=1:1) to give tert-butyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)benzoate (75 mg, 92%) as a solid. LC-MS: 591.2 [M+H]+, tR=1.77 min.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography (silica gel 200-300 mesh, ethyl acetate:petroleum ether=1:1)

Sources & evidence

ORD record
ord-e99e9f1973da408ea01611be8245c656
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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