Potassium Carbonate → 2-(7-Aminonaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

HRID 64515

反応式

HRID 64515 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[S:10][C:9]([C:15]#[N:16])=[N:8][C:7]=1[CH:6]=[CH:5]2.N[C@@H:18]([C:21]([OH:23])=[O:22])[CH2:19][SH:20].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[S:10][C:9]([C:15]3[S:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[N:16]=3)=[N:8][C:7]=1[CH:6]=[CH:5]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 92851D-CysteineHCID 1176042347-Aminonaphtho[2,1-d]thiazole-2-carbonitrile

生成物 1

HCID 862817132-(7-Aminonaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid収率 34.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 7-aminonaphtho[2,1-d]thiazole-2-carbonitrile (24 mg, 0.106 mmol) in acetonitrile was treated with an aqueous solution containing D-cysteine (41 mg, 0.233 mmol) and K2CO3 (45 mg, 0.326 mmol). After stirring at RT for 20 min, the product was isolated by preparative HPLC eluting with a gradient of 5→100% MeCN in 10 mM aqueous NH4OAc. The appropriate fractions were concentrated under reduced pressure and then lyophilized to afford 12 mg of a yellow solid. 1H NMR (DMSO-d6) d 7.77-7.87 (m, 2H); 7.59 (d, 1H); 7.01 (dd, 1H); 6.94 (d, 1H); 5.69 (br s, 2H); 5.18 (t, 1H); 3.57-3.68 (m, 2H).

後処理

  1. customthe product was isolated by preparative HPLC
  2. washeluting with a gradient of 5→100% MeCN in 10 mM aqueous NH4OAc
  3. concentrationThe appropriate fractions were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3b839c8eb02749b09fcccd026a4f54dc
出典データセット
uspto-grants-2016_09
特許番号
US09447450B2

関連ノート

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