Acetic Acid → HCID 23728893, compound

HRID 1944679Notes

Reaction equation

HRID 1944679 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.CC(O)=O.[BH3-]C#N.[Na+]>C1COCC1.CO>[CH:21]1([NH:24][CH2:19][C:17]2[CH:16]=[CH:15][C:13]3[N:14]=[C:10]([N:7]4[CH2:8][CH2:9][N:4]([CH:1]5[CH2:3][CH2:2]5)[CH2:5][CH2:6]4)[S:11][C:12]=3[CH:18]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 59588794HCID 59588794, compound

Product 1

HCID 23728893HCID 23728893, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carbaldehyde (400 mg, 1.39 mmol) and cyclopropylamine (159 mg, 2.78 mmol) in a 1:3 mixture of CH3OH and THF (40 mL) was added AcOH (417 mg, 6.95 mmol), followed by NaCNBH3 (140 mg, 2.22 mmol). The mixture was heated at reflux for 12 h and then the volatiles were evaporated. Water (10 mL) was added and the mixture was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 362 mg (79%) of cyclopropyl-[2-(4-cyclopropylpiperazin-1-yl)-benzothiazol-6-ylmethyl]-amine as a trifluoroacetate salt.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customthe volatiles were evaporated
  4. additionWater (10 mL) was added
  5. extractionthe mixture was extracted with CH2Cl2 (3×15 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by the preparative HPLC

Sources & evidence

ORD record
ord-d2cb938587924f6caeb64c8dcf4b1bba
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

Loading…