Trifluoroacetic acid → N-[6-(2-aminopropanamido)-4-chloropyridin-2-yl]pyridine-2-carboxamide

HRID 1772169Notes

Reaction equation

HRID 1772169 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=[O:28])[NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[O:21])[N:13]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH3:9])[C:10]([NH:11][C:12]1[N:13]=[C:14]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[O:21])[CH:15]=[C:16]([Cl:18])[CH:17]=1)=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117902536tert-butyl-N-(1-{[4-chloro-6-(pyridine-2-amido)pyridin-2-yl]carbamoyl}-ethyl)carbamate

Product 1

HCID 117902638N-[6-(2-aminopropanamido)-4-chloropyridin-2-yl]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-butyl-N-(1-{[4-chloro-6-(pyridine-2-amido)pyridin-2-yl]carbamoyl}ethyl)carbamate K56 (27 mg, 64 μmol) in DCM:TFA=9:1 (3 ml) is stirred at RT for 2 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 12 mg (58%). HPLC-MS: M+H=320; tR=1.57 min (METHOD—1).

Workup

  1. extractionextracted with a saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-4ebe9d5d7f864de0a5c41e0bcb4af43a
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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