Hydrochloric Acid → HCID 67067845、化合物

HRID 1037281

反応式

HRID 1037281 の反応式
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([C:58]5[CH:59]=[N:60][NH:61][CH:62]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:77]>CO.O>[ClH:77].[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([C:58]5[CH:62]=[N:61][NH:60][CH:59]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067908(1-{4-[4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

生成物 1

HCID 67067845HCID 67067845、化合物収率 83%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (7 mL), water (7 mL) and 1 M HCl (0.6 mL) and chromatographed on a 20 g C18 cartridge {gradient 10 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (73 mg, 83%). 1H NMR (400 MHz, DMSO-d6): δ 8.59 (s, 3H), 8.14-8.08 (m, 3H), 7.95 (dd, J=7.9 and 1.8 Hz, 1H), 7.53-7.32 (m, 8H), 7.25 (d, J=8.3 Hz, 2H), 3.83 (bs, 1H), 2.57-2.43 (m, 4H), 2.19-2.06 (m, 1H), 1.82-1.69 (m, 1H). LCMS (Method E): RT=3.03 min, [M+H]+=434.

後処理

  1. customchromatographed on a 20 g C18 cartridge {gradient 10 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

出典と根拠

ORDレコード
ord-f7cae88c4aa54858beb0e5f5d5ca9f3e
出典データセット
uspto-grants-2013_10
特許番号
US08546376B2

関連ノート

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