Hydrochloric Acid → HCID 59252188, compound

HRID 2235640Notes

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-e7cf6bbecc2e4cf6906c5001fcd0d35c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714008B2

Reaction notes

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