1,2,3,4-Tetrahydro-4,4-dimethylisoquinoline → HCID 58386686, compound

HRID 74661Notes

Reaction equation

HRID 74661 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:25]=[CH:24][N:23]=[C:22]([C:26](O)=[O:27])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:29]=1.[CH3:30][C:31]1([CH3:41])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][NH:33][CH2:32]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:30][C:31]1([CH3:41])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][N:33]([C:26]([C:22]2[N:23]=[CH:24][N:25]=[C:20]([N:17]3[CH2:16][CH2:15][CH:14]([N:10]4[CH2:9][CH2:8][C:7]5[CH:29]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=5[NH:12][C:11]4=[O:13])[CH2:19][CH2:18]3)[CH:21]=2)=[O:27])[CH2:32]1

Participants

5

Reactant 3

HCID 1921721,2,3,4-Tetrahydro-4,4-dimethylisoquinolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583866166-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 58386686HCID 58386686, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g mg (0.25 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 57 mg (0.35 mmol) 4,4-dimethyl-1,2,3,4-tetra-hydro-isoquinoline, 75 μL (0.53 mmol) TEA and 0.11 (0.30 mmol) TBTU were stirred in 1.1 mL DMF overnight at RT. The reaction mixture was purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-8a42bedbf4974f04bf6a0297bb4a107f
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…