Hydrochloric Acid → HCID 53242113, compound

HRID 2370339Notes

Reaction equation

HRID 2370339 reaction equation
[ClH:1].C(OC(=O)[NH:8][C@H:9]([C:13](=[O:56])[NH:14][CH2:15][C:16](=[O:55])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([CH:26]2[CH2:31][CH2:30][N:29]([C:32]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]=4[C:43]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)=[O:44])[N:36]([CH2:51][CH2:52][O:53][CH3:54])[CH:35]=3)=[O:33])[CH2:28][CH2:27]2)[CH:20]=1)[CH:10]([CH3:12])[CH3:11])(C)(C)C>O1CCOCC1>[ClH:1].[NH2:8][C@@H:9]([CH:10]([CH3:12])[CH3:11])[C:13]([NH:14][CH2:15][C:16](=[O:55])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([CH:26]2[CH2:31][CH2:30][N:29]([C:32]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]=4[C:43]([N:45]4[CH2:46][CH2:47][O:48][CH2:49][CH2:50]4)=[O:44])[N:36]([CH2:51][CH2:52][O:53][CH3:54])[CH:35]=3)=[O:33])[CH2:28][CH2:27]2)[CH:20]=1)=[O:56]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67262099HCID 67262099, compound

Product 1

HCID 53242113HCID 53242113, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N HCl in dioxane (2.5 mL) was added to ((S)-1-{[(4-fluoro-3-{1-[1-(2-methoxy-ethyl)-4-(morpholine-4-carbonyl)-1H-indole-3-carbonyl]-piperidin-4-yl}-benzylcarbamoyl)-methyl]-carbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester (0.94 mg, 0.12 mmol). The resulting colorless solution was stirred under N2 at rt overnight. The reaction mixture was concentrated in vacuo and the residue was triturated with Et2O (10 mL). The ethereal layer was removed and the pale yellow solid washed with Et2O (3×10 mL). The solid was dried under vacuum to afford the product (85 mg, 99%). 1H NMR (300 MHz, DMSO-d6) δ 8.74-8.71 (m, 1H), 8.54-8.51 (m, 1H), 8.20 (br s, 2H), 7.7.63-7.60 (m, 1H), 7.44-7.36 (m, 1H), 7.32-7.21 (m, 1H), 7.13-7.05 (m, 1H), 7.01-6.98 (d, 1H), 4.39 (t, 2H), 4.25 (d, 2H), 4.21-4.15 (m, 1H), 3.88-3.83 (m, 2H), 3.79-3.77 (m, 1H), 3.69 (t, 2H), 3.62 (br s, 2H), 3.24 (s, 3H), 3.08-2.88 (m, 2H), 2.10-2.03 (m, 1H), 1.85-1.60 (m, 6H), 1.11-1.07 (m, 1H), 0.94 (d, 6H); MS m/z: [M+H]+=679.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was triturated with Et2O (10 mL)
  3. customThe ethereal layer was removed
  4. washthe pale yellow solid washed with Et2O (3×10 mL)
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-5a66012212af41f2a364c25e4ad66913
Source dataset
uspto-grants-2014_04
Patent number
US08710080B2

Reaction notes

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