Hydrochloric Acid → HCID 59252188, compound

HRID 1675300Notes

Reaction equation

[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[BH3-]C#N.[Na+].[CH2:10]([C@H:17]1[CH2:21][O:20][C:19](=[O:22])[N:18]1[C:23](=[O:53])[CH2:24][C@@H:25]([C:31]1[CH:52]=[CH:51][C:34]([O:35][CH2:36][C:37]2[S:41][C:40]([C:42]3[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=3)=[N:39][C:38]=2[CH3:50])=[CH:33][CH:32]=1)[C:26]1[CH:30]=[CH:29][O:28][N:27]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>ClCCCl>[CH2:10]([C@H:17]1[CH2:21][O:20][C:19](=[O:22])[N:18]1[C:23](=[O:53])[CH2:24][C@@H:25]([C:31]1[CH:32]=[CH:33][C:34]([O:35][CH2:36][C:37]2[S:41][C:40]([C:42]3[CH:49]=[CH:48][C:45]([CH2:46][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:44][CH:43]=3)=[N:39][C:38]=2[CH3:50])=[CH:51][CH:52]=1)[C:26]1[CH:30]=[CH:29][O:28][N:27]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Diethylamine (11 μL, 0.11 mmol) and NaCNBH3 (10 mg, 0.16 mmol) were added to a solution of compound 54.4 (54 mg, 0.089 mmol) in DCE (2 mL). The reaction mixture was stirred at 60° C. for 18 hours and then 1N HCl aqueous solution was added. The solution was stirred for 5 minutes and then partitioned between saturated aqueous NaHCO3 solution and DCM. The organic layer was collected, dried over MgSO4 and concentrated in vacuo. The crude product was used without further purification. MS ESI (pos.) m/e: 665 (M+H).

Workup

stirringThe solution was stirred for 5 minutes
custompartitioned between saturated aqueous NaHCO3 solution and DCM
customThe organic layer was collected
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was used without further purification

Sources & evidence

ORD record: ord-010ed83ec69444d08c63206b3f7b3376
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003648B2

Reaction notes

Loading…