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

HRID 1409223노트

반응식

HRID 1409223 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67064333Methyl 1-(4-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-ylcarbamoyl)phenyl)cyclopropanecarboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-21e544b3f3b14dfabde2cd2b8af9a00d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921358B2

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