Serinol → 2-(12-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-ylamino)-propane-1,3-diol

HRID 513767Notes

Reaction equation

HRID 513767 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7](F)=[CH:8][CH:9]=1.[NH2:23][CH:24]([CH2:27][OH:28])[CH2:25][OH:26]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7]([NH:23][CH:24]([CH2:27][OH:28])[CH2:25][OH:26])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 68294SerinolHCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 601647602-(12-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-ylamino)-propane-1,3-diolYield 54%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a similar fashion using route 51 general procedure 118, 12-chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 503 (200 mg, 0.59 mmol), serinol (217 mg, 2.3 mmol) and NMP (2 ml) gave title compound (25 mg, 54%) after purification by column chromatography using DCM/MeOH:aq.NH3 (99.5:0.5:1 drop) as the eluent.

Sources & evidence

ORD record
ord-5a97b8ae1991498cb3045693fc87271d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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