Ammonium Chloride → HCID 178522842, compound

HRID 1625452Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]#[N:20])[CH:18]=[C:13]3[C:12]([C:21]3[CH:22]=[C:23]([CH:44]=[CH:45][CH:46]=3)[CH2:24][NH:25][C:26]([C:28]3[C:29](=[O:43])[N:30]([CH2:34][C:35]4[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=4)[CH:31]=[CH:32][CH:33]=3)=[O:27])=[CH:11]2)(=O)=O)C=CC=CC=1.[N-:47]=[N+:48]=[N-:49].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:47]1[C:19]([C:17]2[CH:18]=[C:13]3[C:12]([C:21]4[CH:22]=[C:23]([CH:44]=[CH:45][CH:46]=4)[CH2:24][NH:25][C:26]([C:28]4[C:29](=[O:43])[N:30]([CH2:34][C:35]5[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=5)[CH:31]=[CH:32][CH:33]=4)=[O:27])=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)=[N:20][N:49]=[N:48]1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(1-benzenesulfonyl-5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide (64 mg, 0.00010 mol) was dissolved in N,N-dimethylformamide (1.0 mL, Acros) and sodium azide (11 mg, 0.00017 mol; Aldrich) and then ammonium chloride (5 mg, 0.00009 mol; Aldrich) was added. The mixture was heated at 110° C. for 1.5 hours under an atmosphere of Argon. Additional sodium azide (29 mg, 0.00045 mol; Aldrich) and ammonium chloride (19 mg, 0.00036 mol; Aldrich) were added and the reaction was heated at 110° C. under an atmosphere of Argon. After 4 h (total), the reaction was diluted with N,N-dimethylformamide, filtered and purified by preparative HPLC to yield the product in 2.0 mg yield (3%). MS m/z=539.07 M+H.

Workup

temperaturethe reaction was heated at 110° C. under an atmosphere of Argon
filtrationfiltered
custompurified by preparative HPLC
customto yield the product in 2.0 mg
customyield (3%)

Sources & evidence

ORD record: ord-aef45a02c78244949302462ce70c2af9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778977B2

Reaction notes

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