Hydrochloric Acid → 1-(4-(7-Morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylic acid

HRID 1409223ノート

反応式

HRID 1409223 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4([C:28]([O:30]C)=[O:29])[CH2:27][CH2:26]4)=[CH:21][CH:20]=3)=[O:18])[CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH:16][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]4([C:28]([OH:30])=[O:29])[CH2:26][CH2:27]4)=[CH:23][CH:24]=3)=[O:18])[CH:8]=2)[CH2:5][CH2:6]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67064333Methyl 1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate2 回

生成物 1

HCID 670645101-(4-(7-Morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylic acid収率 24.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate (Compound 441, 31 mg, 0.07 mmol) was dissolved in methanol, and 1N NaOH solution (1 ml) was then added. After 8 hours at room temperature, the mixture was acidified with 2N HCl to pH 1. The mixture was concentrated in vacuo. The residue was dissolved in DMSO, and was purified by preparatory HPLC (30-65% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound (6.9 mg, 23%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ=12.67-12.24 (m, 1H), 10.98 (s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.98 (d, J=8.3 Hz, 2H), 7.47 (d, J=8.3 Hz, 2H), 7.41 (s, 1H), 6.37 (d, J=2.3 Hz, 1H), 3.85 (m, 2H), 3.74 (m, 2H), 1.56-1.45 (m, 2H), 1.26-1.17 (m, 2H); ESI-MS: m/z 408.4 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in DMSO
  3. customwas purified by preparatory HPLC (30-65% MeCN/H2O gradient+0.01% TFA)

出典と根拠

ORDレコード
ord-21e544b3f3b14dfabde2cd2b8af9a00d
出典データセット
uspto-grants-2014_12
特許番号
US08921358B2

反応ノート

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