Cyclopropylamine → (2S)-2-{[4-({4-[(cyclopropylamino)methyl]phenyl}ethynyl)benzoyl](methyl)amino}-N,2-dimethyl-N'-(tetrahydro-2H-pyran-2-yloxy)propanediamide

HRID 1519710Notes

Reaction equation

HRID 1519710 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:36]=[CH:35][C:14]([C:15]([N:17]([CH3:34])[C@:18]([CH3:33])([C:23]([NH:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[O:24])[C:19]([NH:21][CH3:22])=[O:20])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)=O.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[CH:37]1([NH:40][CH2:1][C:3]2[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]3[CH:12]=[CH:13][C:14]([C:15]([N:17]([CH3:34])[C@:18]([CH3:33])([C:23]([NH:25][O:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][O:28]4)=[O:24])[C:19]([NH:21][CH3:22])=[O:20])=[O:16])=[CH:35][CH:36]=3)=[CH:7][CH:8]=2)[CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 86679270(2S)-2-[{4-[(4-formylphenyl)ethynyl]benzoyl}(methyl)amino]-N,2-dimethyl-N'-(tetrahydro-2H-pyran-2-yloxy)propanediamide

Product 1

HCID 86679276(2S)-2-{[4-({4-[(cyclopropylamino)methyl]phenyl}ethynyl)benzoyl](methyl)amino}-N,2-dimethyl-N'-(tetrahydro-2H-pyran-2-yloxy)propanediamideYield 62%

Procedure

From (2S)-2-[{4-[(4-formylphenyl)ethynyl]benzoyl}(methyl)amino]-N,2-dimethyl-N′-(tetrahydro-2H-pyran-2-yloxy)propanediamide (0.30 g) as obtained in Example 16-(1) and cyclopropylamine (0.19 mL), there was obtained (2S)-2-{[4-({4-[(cyclopropylamino)methyl]phenyl}ethynyl)benzoyl](methyl)amino}-N,2-dimethyl-N′-(tetrahydro-2H-pyran-2-yloxy)propanediamide (white solid) (0.20 g, 62%) in the same manner as in Example 16-(2).

Sources & evidence

ORD record
ord-58a512a8dd0c4ffeaecfa84608989fb3
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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