Morpholine → HCID 67064442, compound

HRID 1409182Notes

Reaction equation

HRID 1409182 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3[CH2:13][CH2:12]3)[CH:10]=[C:6]2[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CN1C(=O)CCC1>CN(C=O)C>[CH:11]1([C:9]2[CH:10]=[C:6]3[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=4)[CH:3]=[C:2]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 86652274HCID 86652274, compound

Product 1

HCID 67064442HCID 67064442, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 2 mL microwave vial was placed N-(7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2J, 100 mg, 0.27 mmol) and morpholine (47.0 mg, 0.54 mmol). To the sealed vial was then added NMP (2 ml) and the mixture was then heated in the microwave at 120° C. for 15 minutes. After cooling to room temperature, DMF (1 ml) was added. The crude product mixture was filtered by syringe filter and purified by preparatory HPLC (35-45% ACN/water, TFA mode). Lyophilization of the collected fractions gave the titled compound product (42 mg, 37% yield) as an off-white powder. 1H NMR (400 MHz, DMSO-d6) δ=10.84 (s, 1H), 7.99 (d, J=8.1 Hz, 2H), 7.59 (d, J=7.8 Hz, 2H), 7.34 (s, 1H), 6.06 (s, 1H), 5.18 (s, 1H), 3.97-3.58 (m, 8H), 2.15-1.96 (m, 1H), 1.45 (s, 5H), 1.08-0.92 (m, 2H), 0.88-0.74 (m, 2H); ESI-MS: m/z 422.2 (M+H)+.

Workup

  1. filtrationThe crude product mixture was filtered by syringe
  2. filtrationfilter
  3. custompurified by preparatory HPLC (35-45% ACN/water, TFA mode)

Sources & evidence

ORD record
ord-c2ae8205cca04ec093d364ed49a5bd6c
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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