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

HRID 1925265Notes

Reaction equation

HRID 1925265 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-742268caa9354a81828f4ec4fb30b6cb
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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