Dimethylsulphamoyl chloride → HCID 69922806, compound

HRID 2416342Notes

Reaction equation

HRID 2416342 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([OH:33])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[C:21]([F:32])[CH:20]=3)=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=2)=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH3:40][N:41]([CH3:46])[S:42](Cl)(=[O:44])=[O:43]>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[C:21]([F:32])[CH:20]=3)=[C:12]([O:33][S:42](=[O:44])(=[O:43])[N:41]([CH3:46])[CH3:40])[CH:11]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 83372Dimethylsulphamoyl chlorideHCID 22636886HCID 22636886, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69922806HCID 69922806, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2,4-Diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3′-fluoro-4′-morpholin-4-ylmethyl-biphenyl-2-ol (250 mg, 0.55 mmol) are [sic] suspended in 11 ml tetrahydrofuran, 0.5 g powdered molecular sieve are added and the mixture is stirred for 15 minutes at room temperature. Potassium tert-butylate (93 mg; 0.83 mmol) is added and the suspension is stirred again for 1 hour at room temperature. The beige suspension is then cooled to −20° C., and N,N-dimethylsulphamoyl chloride (158 mg; 1.1 mmol) is added. The reaction mixture is stirred for 4 hours at 0° C. and 2 hours at 10° C and then concentrated. The residue is chromatographed over silica gel with methylene chloride/MeOH (99:1). 151 mg (49%) dimethylsulphamic acid 4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3′-fluoro-4′-morpholin-4-ylmethyl-biphenyl-2-yl ester are obtained as a light-yellow powder.

Workup

  1. additionare added
  2. stirringthe suspension is stirred again for 1 hour at room temperature
  3. temperatureThe beige suspension is then cooled to −20° C.
  4. stirringThe reaction mixture is stirred for 4 hours at 0° C. and 2 hours at 10° C
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with methylene chloride/MeOH (99:1)

Sources & evidence

ORD record
ord-d4afa3e2210b41bc854846805cea0da0
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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