HCID 59424477, compound → HCID 59424513, compound

HRID 500795Notes

Reaction equation

HRID 500795 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:29][C:28]4[C:23](=[N:24][CH:25]=[CH:26][C:27]=4[O:30][C:31]4[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][C:41](=[O:49])[CH2:42][C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)=[S:39])=[CH:33][C:32]=4[F:50])[CH:22]=3)=[CH:17][CH:16]=2)[CH2:10]1)(C(C)(C)C)(C)C>CC#N.CO.Cl>[F:50][C:32]1[CH:33]=[C:34]([NH:37][C:38]([NH:40][C:41](=[O:49])[CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[S:39])[CH:35]=[CH:36][C:31]=1[O:30][C:27]1[CH:26]=[CH:25][N:24]=[C:23]2[CH:22]=[C:21]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][N:11]4[CH2:12][CH2:13][C@H:9]([OH:8])[CH2:10]4)=[CH:20][CH:19]=3)[S:29][C:28]=12

Participants

4

Reactant 1

HCID 59424477HCID 59424477, compound

Product 1

HCID 59424513HCID 59424513, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 21959252Acetonitrile methanolSolvent

Procedure

To a solution of 103 (34 mg, 0.047 mmol) in CH3CN/MeOH (0.5 mL/2.0 mL), concentrated HCl (8 drops) was added and the reaction was allowed to stir 2 h. The solvents were removed under reduced pressure and the resultant solid was triturated with diethyl ether followed by purification by Gilson HPLC preparative system, column Aquasil C18 (25% MeOH in water to 100% MeOH), to afford title compound 104 (2.5 mg, 9% yield), as a white solid. 1H NMR (DMSO) δ (ppm): 11.82 (1H, s), 8.51 (1H, d, J=5.28 Hz), 8.23 (1H, s), 8.02-7.98 (2H, m), 7.82 (2H, d, J=7.83 Hz), 7.52 (2H, br), 7.41 (2H, d, J=7.83 Hz), 7.33-7.25 (5H, m), 6.64 (1H, d, J=5.09 Hz), 4.20 (1H, br), 3.83 (2H, s), 3.38 (2H, s), 2.34-2.32 (2H, m), 2.03-1.96 (2H, m), 1.56 (2H, br). MS (m/z) 613.3 (M+H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe resultant solid was triturated with diethyl ether
  3. customfollowed by purification by Gilson HPLC preparative system, column Aquasil C18 (25% MeOH in water to 100% MeOH)

Sources & evidence

ORD record
ord-5dfbb5c614eb4f05b7ef03cb0fe3fa6c
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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