Dichloromethane → HCID 11179417, compound

HRID 1833108Notes

Reaction equation

HRID 1833108 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.C(Cl)Cl.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>>[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:18][CH3:19])[C:9]([C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]([N:40]3[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]3)=[O:31])[CH:22]=1)=[N:8][CH:7]=[C:6]2[C:4]([OH:3])=[O:5]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21034870HCID 21034870, compound

Product 1

HCID 11179417HCID 11179417, compoundYield 35%

Procedure

The 1-(3-carboxymethoxybenzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (119 mg, 0.23 mmol) was suspended in 8 ml of methylene chloride containing 10 equivalent of N-methylpiperizine, 1.1 equivalent of HBTU and 4.0 equivalent of triethylamine. The mixture was stirred at room temperature overnight and then evaporated to remove solvents. The residue was extracted with ethyl acetate and water. The organic layer 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 6,7-Dimethoxy-1-{3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-benzoyl}-isoquinoline-4-carboxylic acid as a fluffy solid (39 mg, 35%). ES-MS calcd for C26H27N3O7 (m/e) 493.5, obsd 494.4 (M+H).

Workup

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

Sources & evidence

ORD record
ord-c2c77de8cf5844fdad22cb5b1af098ac
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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