Triethylamine → HCID 11410517, compound

HRID 1833110Notes

Reaction equation

HRID 1833110 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]([OH:31])=O)[CH:22]=2)=[N:8][CH:7]=1)=[O:5])C.[CH2:33]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[CH2:33]([N:40]1[CH2:45][CH2:44][N:43]([C:29](=[O:31])[CH2:28][O:27][C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[C:20]([C:9]2[C:10]3[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[C:6]([C:4]([OH:3])=[O:5])=[CH:7][N:8]=2)=[O:32])[CH2:42][CH2:41]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21034870HCID 21034870, compound

Product 1

HCID 11410517HCID 11410517, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-carboxymethoxybenzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (103.5 mg, 0.22 mmol) in 8 ml of methylene chloride was added 1.0 equivalent of N-benzylpiperazine, 1.05 equivalent of HBTU and 4 equivalent of triethylamine. The mixture was stirred at room temperature overnight. The solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic phase was dried and solvents were evaporated. The residue was dissolved in 4 ml of methanol and aqueous lithium hydroxide was added (0.5N, 1 ml). The mixture was stirred overnight until all starting material disappeared. The reaction was loaded on a preparative HPLC for purification to give 1-{3-[2-(4-Benzyl-piperazin-1-yl)-2-oxo-ethoxy]-benzoyl}-6,7-dimethoxy-isoquinoline-4-carboxylic acid as a fluffy solid (43 mg, 35%). ES-MS calcd for C32H31N3O7 (m/e) 569.6, obsd 570.3 (M+H).

Workup

  1. customThe solvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and water
  3. customThe organic phase was dried
  4. customsolvents were evaporated
  5. dissolutionThe residue was dissolved in 4 ml of methanol
  6. additionaqueous lithium hydroxide was added (0.5N, 1 ml)
  7. stirringThe mixture was stirred overnight until all starting material
  8. customThe reaction was loaded on a preparative HPLC for purification

Sources & evidence

ORD record
ord-4b724aaefc38458baf9f8f70c6d02da6
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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