Thiophene-3-carboxylic acid → N-(6-((6,7-bis(Methoxy)-4-quinolinyl)methyl)-2-naphthalenyl)-3-thiophenecarboxamide

HRID 2115775Notes

Reaction equation

HRID 2115775 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:26])[CH:20]=[CH:19]2.[S:27]1[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26][C:32]([C:29]1[CH:30]=[CH:31][S:27][CH:28]=1)=[O:33])[CH:20]=[CH:19]2

Participants

6

Reactant 4

HCID 6918Thiophene-3-carboxylic acidHCID 8471TriethylamineHCID 2724699PyBOPHCID 675205706-(6,7-Dimethoxy-quinolin-4-ylmethyl)-naphthalen-2-ylamine

Product 1

HCID 59813789N-(6-((6,7-bis(Methoxy)-4-quinolinyl)methyl)-2-naphthalenyl)-3-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(6,7-dimethoxy-quinolin-4-ylmethyl)-naphthalen-2-ylamine (Step g, 36 mg, 0.10 mmol) and 3-thiophenecarboxylic acid (15 mg, 0.115 mmol) in CH2Cl2 (1 mL), was added PyBop (163 mg, 0.314 mmol) and Et3N (44 μL, 0.314 mmol). The mixture was stirred at RT overnight. The solvent was evaporated and the crude material was purified by Prep-TLC with EtOAc/CH2Cl2 (3:2) to give the desired product. MS (ESI, pos. ion) m/z: 455.1 (M+1). Calc'd for C27H22N2O3S: 454.14.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified by Prep-TLC with EtOAc/CH2Cl2 (3:2)

Sources & evidence

ORD record
ord-7a270c23ea604c8fa61c95d2290ede13
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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