Cyclopropanecarboxylic acid → N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide

HRID 1409282Notes

Reaction equation

HRID 1409282 reaction equation
[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]([NH2:16])[CH:8]=2)[CH2:3][CH2:2]1.[CH:17]1([C:20](O)=[O:21])[CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>N1C=CC=CC=1>[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:20]([CH:17]3[CH2:19][CH2:18]3)=[O:21])[CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582073347-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine

Product 1

HCID 44251162N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 0.10 mmol) in pyridine (0.4 ml), cyclopropanecarboxylic acid (0.15 mmol) in pyridine (0.4 ml), HATU (0.17 mmol) in pyridine (0.4 ml) and DIEA (0.34 mmol) are mixed together before microwave irradiation at 150° C. for 6 minutes. The crude product was then purified by preparatory HPLC to give the titled compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.00-1.09 (m, 2H) 1.09-1.16 (m, 2H) 1.99-2.09 (m, 1H) 3.91-3.98 (m, 4H) 4.12-4.21 (m, 4H) 6.47 (d, J=2.26 Hz, 1H) 7.27 (s, 1H) 7.51 (s, 1H) 7.98 (d, J=2.07 Hz, 1H) 13.03 (br. s., 1H); ESI-MS: m/z 288 (M+H)+.

Workup

  1. customThe crude product was then purified by preparatory HPLC

Sources & evidence

ORD record
ord-a2a335113fec4312ae1250a25fad570e
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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