Hydrochloric Acid → HCID 71254456, compound

HRID 540274Notes

Reaction equation

HRID 540274 reaction equation
[O:1]=[S:2]1(=[O:37])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([O:23][CH:24]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:36])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.Cl>C(OCC)(=O)C>[CH3:36][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([N:5]1[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:1])(=[O:37])[CH2:3][CH2:4]1)[CH:22]=[C:21]2[O:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71255391HCID 71255391, compound

Product 1

HCID 71254456HCID 71254456, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 3-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]oxy}pyrrolidine-1-carboxylate (50 mg, 0.096 mmol) and a solution of hydrochloride in ethyl acetate (30 mL, 4 M) was stirred at room temperature for 8 hours. The resulting mixture was concentrated in vacuo and the residue was purified by preparative HPLC and SPE to afford 18.4 mg of the desired product (yield was 45.3%). MS obsd. (ESI+) [(M+H)+] 424, 1H NMR (400 MHz, CD3OD) δ ppm 8.11-8.08 (d, J=6.4 Hz, 1 H), 7.95-7.88 (m, 2 H), 7.78-7.70 (m, 2 H), 7.68-7.56 (m, 2 H), 6.62 (s, 1 H), 5.75-5.70 (m, 1 H), 5.40 (s, 2 H), 4.70-4.50 (m, 2 H), 3.80-3.70 (m, 4 H), 3.65-3.48 (m, 2 H), 2.60-2.50 (m, 1 H), 2.46 (s, 3 H), 2.46-2.35 (m, 1 H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified by preparative HPLC and SPE

Sources & evidence

ORD record
ord-9ba33a2a1c5f4f23ae55bd8b0eeaa53d
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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