Sodium triacetoxyborohydride → n-Cyclopropyl-2,4-difluoro-5-((2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino)benzamide

HRID 1684928Notes

Reaction equation

HRID 1684928 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH:13][CH2:14][C:15]3[CH:16]=[C:17]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:21][C:18]4=[N:19][CH:20]=3)[CH:7]=2)[CH2:3][CH2:2]1.NC1C(F)=CC([F:44])=C(C=1)C(NC1CC1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClCCl>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:7]=[C:8]([NH:13][CH2:14][C:15]3[CH:16]=[C:17]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:21][C:18]4=[N:19][CH:20]=3)[C:9]([F:12])=[CH:10][C:11]=2[F:44])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 219665075-amino-N-cyclopropyl-2,4-difluorobenzamideHCID 59190358n-Cyclopropyl-4-fluoro-3-{(2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino}benzamide

Product 1

HCID 24955944n-Cyclopropyl-2,4-difluoro-5-((2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl)methylamino)benzamideYield 15.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound D of Example 1 (22 mg, 0.1 mmol), in a mixture of acetic acid and dichloromethane (1:1, 1 mL) were added 5-amino-N-cyclopropyl-2,4-difluorobenzamide (30 mg, 0.15 mmol) and NaBH(OAc)3 (30 mg, 0.2 mmol). The mixture was stirred at RT for 1 h. The reaction mixture was concentrated and the residue was purified by preparative RP HPLC. The appropriate fractions were collected and concentrated to remove methanol and saturated solution of NaHCO3 was added to precipitate out the desired product. The solid was filtered and dried in vacuo to give the title compound (6.5 mg) as a solid. LC/MS; (M+H)+=419.2

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative RP HPLC
  3. customThe appropriate fractions were collected
  4. concentrationconcentrated
  5. customto remove methanol and saturated solution of NaHCO3
  6. additionwas added
  7. customto precipitate out the desired product
  8. filtrationThe solid was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-6a9ce568bfd540ca991434a3c8a65bcb
Source dataset
uspto-grants-2012_04
Patent number
US08148361B2

Reaction notes

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