Hydrochloric Acid → HCID 22326757, compound

HRID 495371Notes

Reaction equation

HRID 495371 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]#[N:13])=[CH:4][N:3]=1.[N:14]1([CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl.CCOCC>CC(O)CC>[N:14]1([CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:27]=[CH:28][C:29]([NH:30][C:2]3[N:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[C:5]([C:12]#[N:13])=[CH:4][N:3]=3)=[CH:31][CH:32]=2)(=[O:25])=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22326756HCID 22326756, compoundHCID 22326775HCID 22326775, compound

Product 1

HCID 22326757HCID 22326757, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of 2-chloro-4-isopropoxy-5-cyanopyrimidine (Method 26; 505 mg, 2.56 mmol) and 4-[N-(2-piperidinoethyl)sulphamoyl]aniline (Method 43; 362 mg, 1.28 mmol) in 2-butanol (10 ml) was added 1M HCl in ether (3.6 ml, 3.6 mmol). The reaction was warmed to 70° C. and stirred for 18 hours. The reaction was filtered and the solvent removed under reduced pressure to yield a yellow solid. This solid was partitioned between DCM (40 ml) and 2M sodium hydroxide (40 ml). The phases were separated and the aqueous layer was extracted with DCM (30 ml). The organic phases were combined and washed with water (30 ml) and brine (30 ml). Solvent was removed under reduced pressure and the resulting solid was recrystallized from methanol to give the title compound (15 mg). NMR: 1.35 (m, 2H), 1.45 (m, 10H), 2.25 (m, 6H), 2.85 (m, 2H), 5.45 (m, 1H), 7.30 (br s, 1H), 7.80 (d, 2H), 7.90 (d, 2H),8.75 (s, 1H), 10.60 (br s, 1H); m/z 444.

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent removed under reduced pressure
  3. customto yield a yellow solid
  4. customThis solid was partitioned between DCM (40 ml) and 2M sodium hydroxide (40 ml)
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted with DCM (30 ml)
  7. washwashed with water (30 ml) and brine (30 ml)
  8. customSolvent was removed under reduced pressure
  9. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-69acb2ddd396410cb5bdafa1b11c670d
Source dataset
uspto-grants-2005_09
Patent number
US06939872B2

Reaction notes

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