Hydrochloric Acid → Jtj4sgm9LN

HRID 714569Notes

Reaction equation

HRID 714569 reaction equation
[ClH:1].CC([N:6]([C:10]1([C:16]([NH:18][C@@H:19]([CH2:33][CH3:34])/[CH:20]=[CH:21]/[C:22]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)=[O:23])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)C(=O)[O-])(C)C>C(O)(C)C>[ClH:1].[NH2:6][C:10]1([C:16]([NH:18][C@@H:19]([CH2:33][CH3:34])/[CH:20]=[CH:21]/[C:22]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)=[O:23])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734065HCID 131734065, compound

Product 1

HCID 74766536Jtj4sgm9LNYield 89.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of concentrated aq. HCl (0.23 mL, 2.76 mmol) was added to a solution of 1,1-dimethylethyl[4-({[(1S,2E)-4-(2,3-dihydro-1H-indol-1-yl)-1-ethyl-4-oxo-2-buten-1-yl]amino}carbonyl)tetrahydro-2H-pyran-4-yl]carbamate (251 mg, 0.549 mmol) in isopropanol (2.5 mL). The reaction flask was fitted with an air condenser, and the reaction mixture was heated to 65° C. (bath temp) for 1 h 45 min. The solvent was evaporated under reduced pressure. Water (5 mL) was added to the residue, and the mixture was concentrated under reduced pressure at 65° C. Water (2 mL) was added to the residue, and the mixture was lyophilized, giving 193.3 mg (89%) of the title compound. LC-MS m/z 358 (M+H)+, 0.68 (ret time). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.14 (br. s., 1H); 7.25 (d, J=7.03 Hz, 1H); 7.18 (t, J=7.53 Hz, 1H); 7.02-7.09 (m, 1H); 6.83 (dd, J=15.18, 6.65 Hz, 1H); 6.49 (d, J=14.8 Hz, 1H); 4.56 (d, J=7.28 Hz, 1H); 4.22 (br. s., 2H); 3.95 (d, J=7.53 Hz, 1H); 3.88-3.94 (m, 1H); 3.71-3.78 (m, 2H); 3.23 (br. s., 2H); 2.39-2.46 (m, 2H); 1.79-1.86 (m, 2H); 1.75 (s, 1H); 1.72 (d, J=8.28 Hz, 1H); 1.00 (t, J=7.40 Hz, 3H).

Workup

  1. customThe reaction flask was fitted with an air condenser
  2. customThe solvent was evaporated under reduced pressure
  3. additionWater (5 mL) was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure at 65° C
  5. additionWater (2 mL) was added to the residue

Sources & evidence

ORD record
ord-281de1609b5d429fa1bd48d88f6ca2d8
Source dataset
uspto-grants-2015_11
Patent number
US09187461B2

Reaction notes

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