Hydrochloric Acid → HCID 21934678, compound

HRID 1241393Notes

Reaction equation

HRID 1241393 reaction equation
[H-].[Na+].[N:3]1([C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:17]1[S:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=1.Cl>O.C1COCC1>[N:3]1([C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:17]3[S:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=3)[CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 124618666-(Piperidin-1-yl)pyrimidin-4-amine

Product 1

HCID 21934678HCID 21934678, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A flame dried flask under Ar was charged with sodium hydride (35 mg, 60% dispersion, 0.86 mmol) and 2 mL anhydrous THF. 6-Piperidin-1-yl-pyrimidin-4-ylamine (70 mg, 0.39 mmol) was added slowly followed after 10 minutes by the addition of 2-chloro-thiazole-5-carbonitrile (68 mg, 0.47 mmol). After 1 hour at room temperature the reaction was heated to reflux. After 4 hours, the reaction was cooled, diluted with water and adjusted to pH 7 with 1M HCl (aq). The resulting precipitate was filtered washed with water and air dried. The resulting solid triturated with ether, sonucated, filtered and washed with ether. 1H-NMR (400 MHz, DMSO-d6) 11.99 (s, 1H), 8.39 (1H, s), 8.24 (1H, s), 6.20 (1H, s), 3.57–3.54 (m, 4H), 1.64–1.53 (m, 6H). M+1=287.3. mp>250.

Workup

  1. customA flame dried flask under Ar
  2. temperaturethe reaction was cooled
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and air
  5. customdried
  6. customThe resulting solid triturated with ether
  7. filtrationfiltered
  8. washwashed with ether

Sources & evidence

ORD record
ord-6015ff73722b44ed8bac40708be68906
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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