Ammonium Chloride → HCID 178422277, compound

HRID 879324Notes

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-7af635ba4773421d8ffd2e7fbbb5be8b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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