Triethylamine → 4-(2-piperidinon-1-yl)piperidin-1-yl 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 1432557Notes

Reaction equation

HRID 1432557 reaction equation
CN1CCN=C1C1C=CC([NH:13][C:14]([C@H:16]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][N:17]2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[O:27])=[O:15])=CC=1.ClC1C=CC(NC(C2C3C(=CC=CC=3)CC(C(O)=O)N2)=O)=CC=1.[N:59]1([CH:66]2[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]2)[CH2:64][CH2:63][CH2:62][CH2:61][C:60]1=[O:65].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[N:59]1([CH:66]2[CH2:71][CH2:70][N:69]([CH:18]3[C:19]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:25][CH:16]([C:14]([NH2:13])=[O:15])[N:17]3[C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)=[O:27])[CH2:68][CH2:67]2)[CH2:64][CH2:63][CH2:62][CH2:61][C:60]1=[O:65]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21839852[1,4'-Bipiperidin]-2-oneHCID 57933291(3R)-N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamideHCID 131727716(4-Chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 866065264-(2-piperidinon-1-yl)piperidin-1-yl 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R) 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (50 mg, 0.15 mmol), 4-(2-piperidinon-1-yl) piperidine (20 mg, 0.11 mmol) and triethylamine (30 uL, 0.22 mmol) in DMF (3 mL), BOP (70 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for 30 min. It was then purified by HPLC to give the titled compound (31 mg). MS 495.2 and 497.2 (M+H, Cl pattern).

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-d89b9e16e02844b08496a6acbc5581b5
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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