Diisopropylethylamine → HCID 67064268, compound

HRID 1409212Notes

Reaction equation

HRID 1409212 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9](C)[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.FC(F)(F)C(O)=O.[CH3:32][NH:33][C:34]([C@@H:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1)=[O:35].C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[OH:23][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:4]2[CH:3]=[C:2]([N:38]3[CH2:39][CH2:40][CH2:41][C@@H:36]([C:34]([NH:33][CH3:32])=[O:35])[CH2:37]3)[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=2)=[O:24])=[CH:15][CH:16]=1)([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86652267N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamideHCID 131730620HCID 131730620, compound

Product 1

HCID 67064268HCID 67064268, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 2 mL microwave vial were placed N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 437 mg, 1.3 mmol) and (R)—N-methylpiperidine-3-carboxamide, trifluoroacetate salt (585 mg, 2.2 mmol). To the sealed vial were then added NMP (6 ml) and diisopropylethylamine (0.67 ml, 3.85 mmol), and the mixture was then heated in the microwave at 100° C. for 15 minutes. After cooling to room temperature, the reaction mixture was filtered by syringe filter and was then directly purified by preparatory HPLC (25-50% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (510 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ=10.96 (br. s., 1H), 8.11 (br. s., 1H), 8.00 (d, J=8.1 Hz, 3H), 7.61 (d, J=8.1 Hz, 2H), 7.35 (s, 1H), 6.39 (br. s., 1H), 4.48-4.25 (m, 2H), 3.29 (t, J=11.1 Hz, 1H), 3.08 (br. s., 1H), 2.61 (s, 3H), 2.60 (m, 1H), 2.08 (s, 1H), 1.94 (br. s., 1H), 1.83 (br. s., 1H), 1.73 (br. s., 2H), 1.46 (s, 6H); ESI-MS: m/z 437.4 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered by syringe
  2. filtrationfilter
  3. customwas then directly purified by preparatory HPLC (25-50% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-58b94c6e74394cd7b9bed4f7249e80d3
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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