Diisopropylethylamine → 7-{2-[(2-methoxy-pyridin-4-ylmethyl)-amino]-benzoylamino}-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 969676Notes

Reaction equation

HRID 969676 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=O)[CH:6]=[CH:5][N:4]=1.[C:20]([O:24][C:25]([N:27]1[CH2:36][C:35]([CH3:38])([CH3:37])[C:34]2[C:29](=[CH:30][C:31]([NH2:39])=[CH:32][CH:33]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:20]([O:24][C:25]([N:27]1[CH2:36][C:35]([CH3:38])([CH3:37])[C:34]2[C:29](=[CH:30][C:31]([NH:39][C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10][CH2:9][C:7]3[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=3)=[CH:32][CH:33]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21959561Tert-butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 629894842-[(2-Methoxy-pyridin-4-ylmethyl)-amino]-benzoic acid

Product 1

HCID 695107847-{2-[(2-methoxy-pyridin-4-ylmethyl)-amino]-benzoylamino}-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[(2-methoxy-pyridin-4-ylmethyl)-amino]-benzoic acid (Step A, 516 mg, 2.0 mmol), 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (552 mg, 2.0 mmol), TBTU (0.706 g, 2.2 mmol), and DIEA (0.7 mL) in 30 mL of CH2Cl2 was stirred at RT for 2 h. The mixture was diluted with more CH2Cl2. The organic layer was washed with water, brine, and dried with MgSO4. The solution was filtered, condensed, and the residue was purified by flash column chromatography (0 to 30% of EtOAc in CH2Cl2) to obtain the titled compound as oil. MS (ES+): 517.2 (M+H)+. Calc'd for C30H36N4O4-516.27.

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationThe solution was filtered
  4. customcondensed
  5. customthe residue was purified by flash column chromatography (0 to 30% of EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-72d3ef7d2d9e4b1a99a395f289eb2b26
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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