Hydrochloric Acid → Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

HRID 1622011

Reaction equation

HRID 1622011 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]([N:16]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:16][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86647087Tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate

Product 1

HCID 86647086Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate (0.280 g, 0.686 mmol) in THF (5 mL) was added hydrochloric acid, In (JT Baker) (0.031 mL, 1.030 mmol). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc/sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (135.0 mg). MS (ESI pos. ion) m/z: 244.1. 1H NMR (300 MHz, CDCl3) δ ppm 1.54 (s, 9H) 3.73 (br. s., 2H) 6.93 (br. s., 1H) 7.52 (d, J=2.63 Hz, 1H) 7.94 (d, J=2.63 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc/
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (24 g, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-8bd3a173dbf941afa14831e974a6f03c
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Linked notes

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