Isobutyraldehyde → 3-(3,4-Dichloro-benzenesulfonylamino)-3-(4-fluoro-phenyl)-N-[6-(3-isobutylamino-propyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-propionamide

HRID 32102Notes

Reaction equation

HRID 32102 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:15][C:16](=[O:38])[CH2:17][CH:18]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)(=[O:29])=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:10][CH2:9][CH2:8]2.[CH:39](=O)[CH:40]([CH3:42])[CH3:41].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[Cl:37][C:32]1[CH:31]=[C:30]([S:27]([NH:26][CH:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:17][C:16]([NH:15][CH:11]2[C:12]3[C:7](=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:14][CH:13]=3)[CH2:8][CH2:9][CH2:10]2)=[O:38])(=[O:29])=[O:28])[CH:35]=[CH:34][C:33]=1[Cl:36]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 44216140HCID 44216140, compound

Product 1

HCID 689314983-(3,4-Dichloro-benzenesulfonylamino)-3-(4-fluoro-phenyl)-N-[6-(3-isobutylamino-propyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-propionamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-(3-aminopropyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-3-(3,4-dichloro-benzenesulfonylamino)-3-(4-fluoro-phenyl)-propionamide(63 mg, 0.109 mmol) in dry CH2Cl2 (5 mL) was added isobutyraldehyde (10 μL, 0.109 mmol) and HOAc (1 drop). The resulting mixture was stirred at RT under N2 After 1 h, MS showed the formation of imine; NaBH(OAc)3 (46 mg, 0.218 mmol) was then added. The resulting mixture was stirred for 10 min. The reaction mixture was quenched with sat. NaHCO3. The organic layer was dried over MgSO4 and evaporated in vacuo. The crude solid was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH(2M NH3) mixture (95:5) gave final compound. MS m/z: 635.11 (M+H). Calc'd. for C32H38Cl2FN3O3S-634.63.

Workup

  1. stirringThe resulting mixture was stirred for 10 min
  2. customThe reaction mixture was quenched with sat. NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude solid was purified by chromatography on silica gel
  6. washElution with CH2Cl2

Sources & evidence

ORD record
ord-15d4e48fb94b4c95a02b2bb88cadea3f
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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