Dichloromethane → HCID 66883538, compound

HRID 2359403Notes

Reaction equation

HRID 2359403 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([NH:31][C:32]([C:34]5[N:35]=[CH:36][S:37][CH:38]=5)=[O:33])[CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:47]>>[ClH:47].[N:11]1([CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([NH:31][C:32]([C:34]5[N:35]=[CH:36][S:37][CH:38]=5)=[O:33])[CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58154588HCID 58154588, compound

Product 1

HCID 66883538HCID 66883538, compoundYield 32%

Procedure

Tert-butyl-4-(3-(8-(thiazole-4-carboxamido)quinolin-2-yl)benzyl)piperazine-1-carboxylate from above was treated with a mixture of 25% TFA in CH2Cl2 for 18 hours, concentrated to dryness. The residue was suspended in CH2Cl2, washed with aqueous NaHCO3 (sat.), dried (Na2SO4) and concentrated. The resulting residue was diluted in a minimal amount of dioxane, treated with a slight excess of HCl in methanol, followed by diethyl ether. The resulting HCl salt of N-(2-(3-(piperazin-1-ylmethyl)phenyl)quinolin-8-yl)thiazole-4-carboxamide was collected by filtration. (24 mg 32% yield over two steps). MS (ESI) calcd for C24H23N5OS (m/z): 429.16. found: 430 [M+1].

Workup

  1. concentrationconcentrated to dryness
  2. washwashed with aqueous NaHCO3 (sat.)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionThe resulting residue was diluted in a minimal amount of dioxane
  6. additiontreated with a slight excess of HCl in methanol
  7. filtrationThe resulting HCl salt of N-(2-(3-(piperazin-1-ylmethyl)phenyl)quinolin-8-yl)thiazole-4-carboxamide was collected by filtration

Sources & evidence

ORD record
ord-8a09da85eaa64dfcb0d1173cd11c883e
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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