Water → 4-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide

HRID 1256291Notes

Reaction equation

HRID 1256291 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.[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:16][C:9]2[CH:8]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=2)=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 685154-Bromobenzoyl chlorideHCID 582073347-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine

Product 1

HCID 670644084-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 1.0 g, 4.6 mmol) was suspended in pyridine (10 ml), and 4-bromobenzoyl chloride (1.1 g, 4.8 mmol) was then added at 0° C. After 1 hour, water (200 ml) was added and the resulting precipitate was collected on a fritted glass funnel, washed with water twice, and then dried under a stream of nitrogen for 3 hours to give analytically pure product 4-bromo-N-(7-morpholinopyrazolo[1,5-a]pyrimidin-5-yl)benzamide (9B, 1.6 g, 87%). 1H NMR (400 MHz, DMSO-d6) δ=11.13 (s, 1 H), 8.10 (d, J=2.3 Hz, 1 H), 8.01-7.93 (m, 2 H), 7.77-7.71 (m, 2 H), 7.37 (s, 1 H), 6.38 (d, J=2.3 Hz, 1 H), 3.88-3.81 (m, 4 H), 3.77-3.70 (m, 4 H); ESI-MS: m/z 402.2 (M+H)+.

Workup

  1. customthe resulting precipitate was collected on a fritted glass funnel
  2. washwashed with water twice
  3. customdried under a stream of nitrogen for 3 hours

Sources & evidence

ORD record
ord-4aa20353621c4a85bb73ffa75cdd02e6
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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