Isopropylamine → Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

HRID 887365Notes

Reaction equation

HRID 887365 reaction equation
[C:1]([C:3]1[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[N:15]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:14]=2)=[N:5][C:6](S(C)(=O)=O)=[N:7][CH:8]=1)#[N:2].[CH:43]([NH2:46])([CH3:45])[CH3:44].CCN(C(C)C)C(C)C>C1COCC1>[C:1]([C:3]1[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[N:15]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:14]=2)=[N:5][C:6]([NH:46][CH:43]([CH3:45])[CH3:44])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 68668408Benzyl 3-(5-cyano-2-(methylsulfonyl)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

Product 1

HCID 68668357Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 3-(5-cyano-2-(methylsulfonyl)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (0.826 g, 1.372 mmol) in THF (30 mL) was treated with isopropylamine (0.234 mL, 2.744 mmol, 2.0 Eq) and DIPEA (0.478 mL, 2.744mmol, 2.0 Eq) and allowed to heat at reflux for I hour. The mixture was concentrated in vacuo and purified by column chromatography (ISCO Companion™, 40 g column, 0-100% EtOAc/Petroleum ether) to give 0.651 g (82%) of the title compound.

Workup

  1. temperatureto heat
  2. temperatureat reflux for I hour
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by column chromatography (ISCO Companion™, 40 g column, 0-100% EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-8a79bfdfac124ac8af7d15cb67e2e2fa
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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