Hydrochloric Acid → HCID 71480921, compound

HRID 1622005Notes

Reaction equation

HRID 1622005 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH:12]2[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:6][C:5]([N:15]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:15][C:5]1[CH:6]=[C:7]([NH:8][S:9]([CH:12]2[CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86647084HCID 86647084, compound

Product 1

HCID 71480921HCID 71480921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)cyclopropanesulfonamide (0.300 g, 0.728 mmol) in THF (5 mL) was added hydrochloric acid, In (1.092 mL, 1.092 mmol). The reaction was stirred at rt in closed system. After 30 min, LC/MS showed no sign of starting materials with desired product mass as the major peak. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with more EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 3% MeOH in DCM) to afford the desired product as a yellow solid (170 mg). MS (ESI pos. ion) m/z: 248.0. 1H NMR (300 MHz, CDCL3) δ ppm 1.04 (d, J=6.58 Hz, 2H) 1.13-1.32 (m, 2H) 2.51 (t, J=4.60 Hz, 1H) 3.85 (br. s., 2H) 6.63 (br. s., 1H) 7.35 (s, 1H) 7.68 (s, 1H).

Sources & evidence

ORD record
ord-b86cfa8a61564a4188abb32694563d4e
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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