Hydrochloric Acid → HCID 136344401, compound

HRID 62222Notes

Reaction equation

HRID 62222 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:24]=[C:7]2[N:8]=[C:9]([C:16]3[C:17]([CH3:23])=[N:18][N:19]([CH2:21]C)[CH:20]=3)[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:6]2[N:5]=1.Cl>C(O)C>[Br:3][C:4]1[CH:24]=[C:7]2[NH:8][CH:9]([C:16]3[C:17]([CH3:23])=[N:18][N:19]([CH3:21])[CH:20]=3)[CH2:10][CH:11]([C:12]([F:13])([F:14])[F:15])[N:6]2[N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 867041792-bromo-5-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 136344401HCID 136344401, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium tetrahydroborate (472 mg) was slowly added to a suspension of 2-bromo-5-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Preparation 7, 1.8 g) in Ethanol (20 mL). The reaction mixture was stirred at room temperature for 3 hours. The reaction solution was then very slowly added to ice cooled 1N HCl until a pH=2.0 was achieved to quench any remaining sodium tetrahydroborate. The solution was then concentrated under high vacuum to remove the majority of ethanol. Saturated sodium bicarbonate aqueous solution was then slowly added to the acidic solution until a neutral pH (7.0) was achieved and a white precipitate forms. The precipitate was filtered off and washed with water (200 mL) and ether (20 mL). The white precipitate was collected and dried in vacuo to afford the title compound as a white powder (1.36 g, 74.7%). 1H NMR (400 MHz, DMSO-d6) δ: 2.00, (m, 1H), 2.09, (s, 3H), 2.30, (m, 1H), 3.67, (s, 3H), 4.34, (m, 1H), 5.15, (m, 1H), 5.31, (s, 1H), 6.69, (s, 1H), 7.63, (s, 1H).

Workup

  1. additionThe reaction solution was then very slowly added to ice
  2. customto quench any remaining sodium tetrahydroborate
  3. concentrationThe solution was then concentrated under high vacuum
  4. customto remove the majority of ethanol
  5. additionSaturated sodium bicarbonate aqueous solution was then slowly added to the acidic solution until a neutral pH (7.0)
  6. filtrationThe precipitate was filtered off
  7. washwashed with water (200 mL) and ether (20 mL)
  8. customThe white precipitate was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-6fc2cb6fd89b4fd79f53a2b916b1aa7d
Source dataset
uspto-grants-2016_09
Patent number
US09446046B2

Reaction notes

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