Diisopropylcarbodiimide → HCID 69915132, compound

HRID 402466Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:21][CH2:22][C:23](O)=[O:24])=[CH:14][C:15]=2[C:17]([F:20])([F:19])[F:18])[N:10]([CH3:26])[N:9]=1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:46][C@H:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:21][CH2:22][C:23]([NH:54][C@H:47]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH3:46])=[O:24])=[CH:14][C:15]=2[C:17]([F:20])([F:18])[F:19])[N:10]([CH3:26])[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-(3-(2-fluorophenyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetic acid (70 mg, 0.189 mmol), DIC (31.1 mg, 0.246 mmol) and HOBt (38.4 mg, 0.285 mmol) in DMF (3 ml) was stirred at rt for 15 min. (S)-(−)-α-methyl benzyl amine (25.3 mg, 0.208 mmol) was added dropwise to the reaction mixture at rt and then the mixture was heated at 100° C. for 1 h. After completion of the reaction, ice-cold water was added and the reaction mixture was stirred for 10 min. The resulting precipitate was collected by filtration. The crude product was re-crystallized from diethyl ether to yield 46 mg (51%) of the title compound. [1H-NMR (CDCl3, 300 MHz) δ 7.55-7.05 (m, 9H), 7.01 (s, 1H), 6.55 (d, 1H), 5.23 (m, 1H), 5.01 (s, 2H), 4.03 (s, 3H), 1.60 (d, 3H); HPLC RtA=5.384 min (98%); LCMS RtD=3.055; [M+H]+=473.1].

Workup

additionwas added dropwise to the reaction mixture at rt
customAfter completion of the reaction, ice-cold water
additionwas added
filtrationThe resulting precipitate was collected by filtration
customThe crude product was re-crystallized from diethyl ether

Sources & evidence

ORD record: ord-e50f517a42814fe29b8606b2ffcd8f96
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742106B2

Reaction notes

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