Triethylamine → HCID 178458106, compound

HRID 1013007Notes

Reaction equation

HRID 1013007 reaction equation
[NH2:1][C:2]([C:5]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2S(C)(=O)=O)=[O:12])[C:8]([OH:26])=[C:7]([OH:27])[N:6]=1)([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:35][CH2:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[Cl:35][CH2:36][S:37]([O:26][C:8]1[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:12])=[N:10][C:5]([C:2]([NH:1][S:37]([CH2:36][Cl:35])(=[O:39])=[O:38])([CH3:4])[CH3:3])=[N:6][C:7]=1[OH:27])(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 8471Triethylamine3×HCID 77054(Chloromethyl)sulfonyl chloride3×HCID 178456882HCID 178456882, compound

Product 1

HCID 178458106HCID 178458106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide hydrochloride (prepared as described in WO2003035076 A1) in dichloromethane, triethylamine (4 eq.) was added and the mixture was cooled down with an ice/salt bath. A solution of chloromethanesulfonyl chloride in dichloromethane was added dropwise to the mixture. After 2 hours further triethylamine (1 eq.) and chloromethanesulfonyl chloride (1 eq.) were added at 0° C. and the reaction mixture was aged at room temperature overnight. To allow complete consumption of starting material, additional Et3N (0.5 eq.) and chloromethanesulfonyl chloride (0.5 eq.) were added at 0° C. After one hour, the mixture was poured in dichloromethane and washed with 1N HCl and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to obtain title compound as yellow oil. 1H NMR (300 MHz, d6-DMSO) δ 13.32 (bs, 1H), 9.19 (t, J=6.0 Hz, 1H), 8.03 (s, 1H), 7.37 (dd, J=8.4 Hz, J=5.7 Hz, 2H), 7.15 (t, J=8.5 Hz, 2H), 5.59 (s, 2H), 4.86 (s, 2H), 4.45 (d, J=6.2 Hz, 2H), 1.64 (s, 6H); MS (ES) C17H19Cl2FN4O7S2 requires 545. Found: 546 (M+H+).

Workup

  1. temperaturethe mixture was cooled down with an ice/salt bath
  2. additionwere added at 0° C
  3. waitAfter one hour
  4. washwashed with 1N HCl and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e98f1ddabc1492a96dd86b63eb1f25b
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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