Ammonium Chloride → HCID 178422277, compound

HRID 510311Notes

Reaction equation

[C:1]([O:7][CH2:8][C@@H:9]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl-].[NH4+].[N-:48]=[N+:49]=[N-:50].[Na+]>CN(C=O)C>[C:1]([O:7][CH2:8][C@H:9]([C:10]1[C:32]([CH3:33])=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[NH:50][N:49]=[N:48][N:30]=5)[CH:24]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3-cyanophenyl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate (17.2 mg, 0.027 mmol) in DMF (0.5 mL) was added ammonium chloride (7.2 mg, 0.135 mmol) and sodium azide (9.4 mg, 0.144 mmol). The reaction mixture was heated at 120° C. for 6 h then cooled. The crude reaction mixture was passed through a silica gel plug (hexanes/ethyl acetate eluent) to remove the DMF and salts, concentrated, and used without further purification. LCMS-ESI+: calc'd for C37H38ClN6O3S: 681.2 (M+H+); Found: 680.9 (M+H+).

Workup

temperaturethen cooled
customThe crude reaction mixture
customto remove the DMF and salts
concentrationconcentrated
customused without further purification

Sources & evidence

ORD record: ord-caba19ba29054f2db45b2e3dc1448a4d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096586B2

Reaction notes

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