Hydrochloric Acid → [4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid

HRID 348496Notes

Reaction equation

HRID 348496 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:40])[CH2:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([N:26]=[N+:27]=[N-:28])=[CH:22][CH:21]=2)[C:12]([C:30](=[O:39])[NH:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:11][N:10]=1)C.Cl>C1COCC1>[N:26]([C:23]1[CH:22]=[CH:21][C:20]([C:19]([NH:18][CH2:17][CH2:16][NH:15][C:13]2[C:12]([C:30](=[O:39])[NH:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:11][N:10]=[C:9]([S:8][CH2:7][C:6]([OH:40])=[O:5])[N:14]=2)=[O:29])=[CH:25][CH:24]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86760402[4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

Product 1

HCID 21087397[4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acidYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M NaOH (0.5 mL, 0.5 mmol) was added to a solution of [4-[2-(4-Azido-benzoylamino)-ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (8 mg, 0.015 mmol) in THF (0.5 mL) at ambient temperature. The reaction was stirred for 1 h, then acidified with 1 N HCl to pH 3. The reaction mixture was concentrated by rotary evaporation, and the resulting solid was filtered, washed with water and dried to yield the titled product (4 mg, 53%) as a white solid. 1H NMR: (d6-DMSO) δ 10.22 (s, 1H), 8.63 (m, 1H), 8.56 (s, 1H), 7.82 (d, 2H), 7.60 (m, 2H), 7.13 (m, 3H), 3.89 (s, 2H), 3.62 (m, 2H), 3.34 (m, 2H); HPLC: Rt=4.13 min; MS (ESI): m/z 509.07 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. filtrationthe resulting solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-67257b6eedc444e3bdffe27d80560be1
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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