Diisopropylethylamine → HCID 68065850, compound

HRID 2044069Notes

Reaction equation

[C:1]([C:4]1[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[N:6][C:7](Cl)=[CH:8][CH:9]=1)(=[O:3])[NH2:2].[NH:34]1[CH2:39][CH2:38][CH2:37][C@@H:36]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:35]1.CCN(C(C)C)C(C)C>CN1CCCC1=O>[C:43]([O:42][C:41]([NH:40][C@@H:36]1[CH2:37][CH2:38][CH2:39][N:34]([C:7]2[N:6]=[C:5]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:25])[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[C:4]([C:1](=[O:3])[NH2:2])=[CH:9][CH:8]=2)[CH2:35]1)=[O:47])([CH3:46])([CH3:44])[CH3:45]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of benzyl 4-(4-(3-carbamoyl-6-chloropyridin-2-ylamino)phenyl)piperazine-1-carboxylate (4 g, 8.58 mmol), (R)-tert-butyl piperidin-3-ylcarbamate (2.58 g, 12.88 mmol), and DIEA (3.00 mL, 17.17 mmol) in N-methyl-2-pyrrolidinone (6 mL) was placed in two capped scintillation vials and heated at 100° C. overnight. The reaction mixtures were quenched with water and filtered. The solid was purified by MPLC chromatography (ISCO, 6% NH4OH/MeOH/CH2Cl2, two 40 g stacked silica gel columns) to give 4.71 g of ((R)-benzyl 4-(4-(6-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-3-carbamoylpyridin-2-ylamino)phenyl)piperazine-1-carboxylate).

Workup

customThe reaction mixtures
customwere quenched with water
filtrationfiltered
customThe solid was purified by MPLC chromatography (ISCO, 6% NH4OH/MeOH/CH2Cl2, two 40 g stacked silica gel columns)

Sources & evidence

ORD record: ord-9744115b09154ee9a54752f371ee0c54
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586751B2

Reaction notes

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