Ammonium Chloride → HCID 66707458, compound

HRID 2041598Notes

Reaction equation

[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:20]2[C:23]([S:28][CH2:29][C:30]3[CH:31]=[N:32][C:33](Cl)=[CH:34][CH:35]=3)=[C:24]([Cl:27])[CH:25]=[CH:26][C:19]=2[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>CCOC(C)=O>[C:9]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:20]2[C:23]([S:28][CH2:29][C:30]3[CH:31]=[N:32][C:33]([NH:8][CH2:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:34][CH:35]=3)=[C:24]([Cl:27])[CH:25]=[CH:26][C:19]=2[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 170 °C

Procedure

Add cyclohexylmethylamine (3 mL) to a flask containing 3-tert-butoxycarbonyl-7-chloro-6-(6-chloro-pyridin-3-ylmethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (340 mg, 0.8 mmol) and ammonium chloride (50 mg, 0.92 mmol). Heat the contents in a sealed flask at 170° C. for 7 h. Cool the flask to room temperature, dilute with EtOAc (50 mL) and wash with water (20 mL). Collect the organic layer and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (19:1 to 4:1 gradient) to obtain 3-tert-butoxycarbonyl-7-chloro-6-(6-cyclohexylmethylamino-pyridin-3-ylmethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (160 mg, 40%).

Workup

temperatureCool the flask to room temperature
washwash with water (20 mL)
customCollect the organic layer
concentrationconcentrate in vacuo
customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (19:1 to 4:1 gradient)

Sources & evidence

ORD record: ord-3d4eb6e02190483bae0be08745bbac3f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580780B2

Reaction notes

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