Diisopropylethylamine → (R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

HRID 516081Notes

Reaction equation

HRID 516081 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1.[NH2:22][CH2:23][C@@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][O:26][CH3:27].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:31]([O:30][C:29]([NH:28][C@@H:24]([CH2:25][O:26][CH3:27])[CH2:23][NH:22][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1)=[O:35])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 58317587Methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinateHCID 59199768tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamate

Product 1

HCID 67238996(R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(m-tolylamino)nicotinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a screw-top vial was added methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinate (0.28 g, 0.928 mmol), (R)-tert-Butyl 1-amino-3-methoxypropan-2-ylcarbamate (0.227 g, 1.114 mmol), and DIPEA (0.211 mL, 1.206 mmol) in DMF (3 mL). The resulting yellow solution was stirred at RT for 12 h, diluted with EtOAc (30 mL) and washed with water (2×20 mL) and brine (20 mL). The organic phase was dried with Na2SO4 and concentrated to give the title compound as thick yellow oil, which was used without further purification (470 mg). [M+H] calc'd for C24H31N5O5, 470; found, 470.

Workup

  1. washwashed with water (2×20 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c901a8bd8f9c404eafdc4a12b514006d
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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