Hydrochloric Acid → (S)-2-azido-1-(3-fluoro-5-iodophenyl)ethanamine hydrochloride salt

HRID 596001ノート

反応式

HRID 596001 の反応式
OC(C(F)(F)F)=O.NC1C(C2C=CC(C(O)=O)=C(F)C=2)=NC(C2CCOCC2)=CN=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:50]([CH2:53][C@@H:54]([NH:63]C(=O)OC(C)(C)C)[C:55]1[CH:60]=[C:59]([I:61])[CH:58]=[C:57]([F:62])[CH:56]=1)=[N+:51]=[N-:52].[ClH:71]>CN(C=O)C.O1CCOCC1>[ClH:71].[N:50]([CH2:53][C@H:54]([C:55]1[CH:60]=[C:59]([I:61])[CH:58]=[C:57]([F:62])[CH:56]=1)[NH2:63])=[N+:51]=[N-:52]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 118054631(S)-tert-butyl (2-azido-1-(3-fluoro-5-iodophenyl)ethyl)carbamateHCID 1317346124-(3-Amino-6-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yl)-2-fluorobenzoic acid TFA

生成物 1

HCID 118045365(S)-2-azido-1-(3-fluoro-5-iodophenyl)ethanamine hydrochloride salt

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

実験手順

4-(3-Amino-6-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yl)-2-fluorobenzoic acid TFA adduct (126 mg, 0.292 mmol) and HOAt (0.060 g, 0.438 mmol) was dissolved in DMF (1 mL) and DIEA (0.156 mL, 0.876 mmol). (S)-2-azido-1-(3-fluoro-5-iodophenyl)ethanamine hydrochloride salt (100 mg, 292 mmol), obtained from the reaction of (S)-tert-butyl (2-azido-1-(3-fluoro-5-iodophenyl)ethyl)carbamate with 4M HCl in dioxane (Step 9 in Scheme 76), was added, followed by EDC (0.090 g, 0.467 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and water, and the organic layer was washed with water twice and then with saturated Na2CO3. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo providing crude (S)-4-(3-amino-6-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yl)-N-(2-azido-1-(3-fluoro-5-iodophenyl)ethyl)-2-fluorobenzamide without further purification.

出典と根拠

ORDレコード
ord-db05d60599b54d368b0ff5514a378e87
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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