Hydrochloric Acid → HCID 69926998, compound

HRID 1421685Notes

Reaction equation

HRID 1421685 reaction equation
[ClH:1].Cl.Cl.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH:27]=3)[CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[CH3:40][CH2:41][OH:42].CCOCC>CCOCC>[ClH:1].[C:41]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[CH:14][C:15]([C@@H:18]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH:27]=3)[CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)(=[O:42])[CH3:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21585056Diethyl ether ethanolHCID 21969138HCID 21969138, compound

Product 1

HCID 69926998HCID 69926998, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Treatment of the free base (303.6 mg) in EtOH-Et2O (30 ml; 1:2) with 1.0M HCl in Et2O (0.62 ml) as described for the compound of Example 7 followed by the recrystallisation (THF-Et2O) afforded the title compound as an off-white amorphous solid (highly hygroscopic). δH (CD3OD) 1.50-1.90 (8H, br m), 2.11 (3H, s), 3.67 (2H, d, J 8.3 Hz), 3.76 (3H, s), 4.40 (1H, t, J 8.3 Hz), 4.73 (1H, br m), 6.79 (1H, s), 6.83 (1H, s), 6.84 (1H, s), 6.85-6.95 (4H, m), 7.28 (2H, d, (fine split), J 8.5 Hz), 7.50 (2H, dd, J 6.9, 2.3 Hz), 7.80 (2H, d, J 6.4 Hz), and 8.60 (2H, d, J 5.9 Hz).

Workup

  1. customfollowed by the recrystallisation (THF-Et2O)

Sources & evidence

ORD record
ord-c4c8994e6d524796b7d76d60ea192ec9
Source dataset
uspto-grants-2000_06
Patent number
US06077854

Reaction notes

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