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Trifluoroacetic acid → 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide

HRID 1802010
ノート
印刷プレビュー

反応式

HRID 1802010 の反応式
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=O)OC(C)(C)C.N1(OC2[N:31]=[C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]4[N:40]=[CH:41][S:42][CH:43]=4)=[C:35]([F:44])[CH:34]=3)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=2)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[N:40]=[CH:41][S:42][CH:43]=3)=[C:35]([F:44])[CH:34]=2)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 574718832-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxamide

生成物 1

HCID 574718782-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide
収率 43.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.30 M in NMP, 1.00 mL, 0.300 mmol) in NMP (1 mL) was added to 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxamide (12 mg, 0.027 mmol). DIEA (0.050 mL, 0.29 mmol) was also added. The mixture was stirred at 90 C for 1 h. After being cooled to room temperature, TFA (1 mL) was added. The solution was stirred at room temperature for 60 min. The mixture was purified by HPLC to give the titled compound (5 mg). MS 428.4 (M+H). UV λ=229.8, 313.8 nm.

後処理

  1. stirringThe solution was stirred at room temperature for 60 min
  2. customThe mixture was purified by HPLC

出典と根拠

ORDレコード
ord-be15d7da394f4e7787ea67f408d4871d
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08349860B2

反応ノート

読み込み中…

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