Cyclopropanecarboxylic acid → HCID 44251162, compound

HRID 1256437Notes

Reaction equation

HRID 1256437 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 44251162HCID 44251162, compound

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, 2 H) 1.09-1.16 (m, 2 H) 1.99-2.09 (m, 1 H) 3.91-3.98 (m, 4 H) 4.12-4.21 (m, 4 H) 6.47 (d, J=2.26 Hz, 1 H) 7.27 (s, 1 H) 7.51 (s, 1 H) 7.98 (d, J=2.07 Hz, 1 H) 13.03 (br. s., 1 H); ESI-MS: m/z 288 (M+H)+.

Workup

  1. customThe crude product was then purified by preparatory HPLC

Sources & evidence

ORD record
ord-f6e7e7062b8d462d880801d5478f0a0e
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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