Hydrochloric Acid → HCID 67491262, compound

HRID 1952460Notes

Reaction equation

HRID 1952460 reaction equation
Cl.[F:2][C:3]1[CH:37]=[C:36]([NH:38][C:39]([N:41]2[CH2:45][CH2:44][N:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:42]2=[O:52])=[O:40])[CH:35]=[CH:34][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]3[N:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:30][CH2:31][O:32][CH3:33])C(=O)OC(C)(C)C)=[CH:17][CH:16]=3)[S:14][C:7]=12>C(Cl)Cl>[F:2][C:3]1[CH:37]=[C:36]([NH:38][C:39]([N:41]2[CH2:45][CH2:44][N:43]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:42]2=[O:52])=[O:40])[CH:35]=[CH:34][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][NH:22][CH2:30][CH2:31][O:32][CH3:33])=[CH:19][N:20]=3)[S:14][C:7]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71027919HCID 71027919, compound

Product 1

HCID 67491262HCID 67491262, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl gas was bubbled into a solution of 127 (61 mg, 0.08 mmol) in DCM. The flask was capped and the mixture was stirred at room temperature for 30 min. Formed precipitate was collected by filtration and washed with DCM to afford 128 (52 mg, 84% yield), presumably as a trihydrochloride salt. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.59 (s, 1H), 9.34 (br.s, 2H), 8.75 (s, 1H), 8.62 (d, J=5.7 Hz, 1H), 8.43 (s, 1H), 8.38 (d, J=8.5 Hz, 1H), 8.15 (dd, J=8.2, 2.1 Hz, 1H), 7.86 (dd, J=12.9, 2.4 Hz, 1H), 7.62 (d, J=7.6 Hz, 2H), 7.4-7.6 (m, 4H), 7.17 (t, J=7.3 Hz, 1H), 6.81 (d, J=5.5 Hz, 1H), 4.25 (m, 2H), 3.95 (m, 4H), 3.62 (m, 2H), 3.29 (s, 3H), 3.13 (br.s, 2H). MS (m/z): 613.3 (M+H).

Workup

  1. customThe flask was capped
  2. customFormed precipitate
  3. filtrationwas collected by filtration
  4. washwashed with DCM

Sources & evidence

ORD record
ord-d31c7b383fb24538acb18324f2706e48
Source dataset
uspto-grants-2013_03
Patent number
US08404846B2

Reaction notes

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